Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[CH2:14]Br)[CH3:2].[CH3:17][C:18]([SH:21])([CH3:20])[CH3:19].[H-].[Na+]>CC#N>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[CH2:14][S:21][C:18]([CH3:20])([CH3:19])[CH3:17])[CH3:2]
Reactant: CC(C)(C)S
Reactant: CCOC(=O)c1ccc([N+](=O)[O-])cc1CBr
Agent: [H-]
Agent: [Na+]
Solvent: CC#N
Product: CCOC(=O)c1ccc([N+](=O)[O-])cc1CSC(C)(C)C
Temperature: 0 °C
Reaction time: 0.08 h

Procedure:
2-Bromomethyl-4-nitro-benzoic acid ethyl ester (8.0 g, 27.8 mmol) and 2-methyl-2-propanethiol (3.74 mL, 33.3 mmol) were combined in MeCN (100 mL) at 0° C. Sodium hydride (60% in mineral oil; 1.39 g, 34.8 mmol) was added, and the reaction was stirred for 5 minutes at 0° C., and then at room temperature until no starting material was seen by analytical tlc. The mixture was quenched by adding ice chips and diluted with H2O (100 mL) and 1N aqueous HCl (30 mL), and then extracted with EtOAc. The combined organic layers were washed with H2O, dried, filtered, and concentrated, and the residue was purified by silica gel chromatography to give the title compound.
Reaction SMILES: [C:1]1([CH2:10][C:11]#[N:12])[CH:6]=[CH:5][C:4]([CH2:7][C:8]#[N:9])=[CH:3][CH:2]=1.N.[H][H]>[Ni].CO>[NH2:9][CH2:8][CH2:7][C:4]1[CH:5]=[CH:6][C:1]([CH2:10][CH2:11][NH2:12])=[CH:2][CH:3]=1
Reactant: N#CCc1ccc(CC#N)cc1
Reactant: [H][H]
Agent: [Ni]
Agent: N
Solvent: CO
Product: NCCc1ccc(CCN)cc1
Temperature: 25 °C
Yield: 98 %

Procedure:
Scheme I, step B′: Into a 250 mL reduction vessel were placed 1,4-phenylenediacetonitrile (10 g, 64.02 mmol), liquid ammonia (25 mL), and W4-W6 range (medium range activity) Raney Nickel (1.25 g) in methanol (125 mL), and the mixture was heated at 100° C. under 300 psi (2068 kPa) of hydrogen gas for 10 hours. The reaction was cooled to room temperature and filtered through a Celite® cake and the filtrate was concentrated under reduced vacuum to give the intermediate title compound, 2-[4-(2-aminoethyl)phenyl]ethylamine, (10.3 g, 98%) as an oil. Electron spray M.S. 165 (M*+H).
Reaction SMILES: [C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[C:9](Br)=[N:10][CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18]>C(N(CC)CC)C.CN(C=O)C.C(OCC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[C:9]([C:21]#[C:20][Si:17]([CH3:19])([CH3:18])[CH3:16])=[N:10][CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2]
Reactant: CC(C)(C)OC(=O)Nc1cccnc1Br
Reactant: C#C[Si](C)(C)C
Agent: Cl[Pd](Cl)([P](c1ccccc1)(c1ccccc1)c1ccccc1)[P](c1ccccc1)(c1ccccc1)c1ccccc1
Agent: [Cu]I
Solvent: CN(C)C=O
Solvent: CCN(CC)CC
Solvent: CCOCC
Product: CC(C)(C)OC(=O)Nc1cccnc1C#C[Si](C)(C)C
Temperature: 25 °C
Reaction time: 8 h
Yield: 43 %

Procedure:
A mixture of (2-bromopyridin-3-yl)carbamic acid tert-butyl ester (1.09 mg, 4.00 mmol), (trimethylsilyl)acetylene (2.83 mL, 20.0 mmol), CuI (75.8 mg, 0.400 mmol), and dichlorobis(triphenylphosphine)palladium (II) (141 mg, 0.200 mmol) in a mixture of 12 mL of triethylamine and 3.0 mL of anhydrous DMF were stirred at room temperature overnight. The reaction was diluted with 50 mL of diethyl ether and quenched with 50 mL of saturated aqueous ammonium chloride solution. The organic layer was washed with 20 mL of saturated aqueous ammonium chloride solution and the combined aqueous layers were extracted with three 20 mL portions of diethyl ether. The combined organic layers were then washed with 20 mL of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. Chromatography on SiO2 (20% to 30% ethyl acetate in hexanes, gradient) gave 500 mg of (2-trimethylsilanylethynylpyridin-3-yl)carbamic acid tert-butyl ester (43% yield).
Reaction SMILES: [S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([C:13]1[CH:18]=[CH:17][N:16]=[C:15](Cl)[N:14]=1)[C:11]#[N:12].C([O-])(=O)C.[Na+]>C(O)(=O)C.[Pd]>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][N:14]=1)[C:11]#[N:12]
Reactant: N#CC(c1ccnc(Cl)n1)c1nc2ccccc2s1
Agent: [Pd]
Agent: CC(=O)[O-]
Agent: [Na+]
Solvent: CC(=O)O
Product: N#CC(c1ccncn1)c1nc2ccccc2s1
Temperature: 70 °C
Yield: 13.6 %

Procedure:
To a solution of 1 (0.1 g, 0.35 mmol) in acetic acid was added sodium acetate (29 mg, 0.35 mmol) and palladium on charcoal (20 mg). The suspension was heated up to 70° C. under hydrogen at 3.5 bar for 3 h. After cooling to r.t., the suspension was filtered through celite and the acetic acid evaporated. The bright yellow powder was taken up in ethyl acetate and aqueous sodium hydroxide 10%. After 3 extractions the organic phases were thoroughly washed with brine then dried over MgSO4 and concentrated to dryness. After purification by preparative HPLC and drying under vacuum at 50° C., 12 mg (13%) of the title compound were obtained as a yellow powder.
Reaction SMILES: [OH:1][C@@H:2]([CH3:20])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[N:14]([CH3:18])[CH:13]=[N:12][C:11]=2[N:10]([CH3:19])[C:8]1=[O:9].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>ClCCl>[CH3:28][S:29]([O:1][C@@H:2]([CH3:20])[CH2:3][CH2:4][CH2:5][CH2:6][N:7]1[C:16](=[O:17])[C:15]2[N:14]([CH3:18])[CH:13]=[N:12][C:11]=2[N:10]([CH3:19])[C:8]1=[O:9])(=[O:31])=[O:30]
Reactant: CS(=O)(=O)Cl
Reactant: C[C@H](O)CCCCn1c(=O)c2c(ncn2C)n(C)c1=O
Solvent: ClCCl
Solvent: CCN(CC)CC
Product: C[C@@H](CCCCn1c(=O)c2c(ncn2C)n(C)c1=O)OS(C)(=O)=O
Temperature: 0 °C
Reaction time: 4 h

Procedure:
A solution of (S)-1-(5-hydroxyhexyl)-3,7-dimethylxanthine (Klein, J. P.; Leigh, A, J.; Michnick, J.; Kumar, A. M.; Underiner, G. E. Asymmetric Synthesis of Chiral Secondary Alcohols, U.S. Pat. No. 5,629,423 (May 13, 1997)) (14 g, 50 mmol) and triethylamine (14 ml) was cooled to 0° C. in dichloromethane (200 ml) and methanesulfonyl chloride (5.80 ml. 75 mmol) was added slowly at 0° C. After stirring for an additional 4 hours at 0° C., the reaction was quenched by the addition of water and extracted with dichloromethane (4x 150 ml). The combined extracts were washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to provide (S)-1-(5-methanesulfonyloxyhexyl)-3,7-dimethylxanthine (19.6 g).
Reaction SMILES: [O:1]1[CH2:16][CH:2]1[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[CH:7][CH:6]=1.[CH2:17]([NH:24][CH2:25][CH2:26][O:27][C:28]1[CH:36]=[C:32]([C:33]([NH2:35])=[O:34])[C:31]([OH:37])=[CH:30][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)(C)C>[CH2:17]([N:24]([CH2:25][CH2:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([OH:37])=[C:32]([C:33](=[O:34])[NH2:35])[CH:36]=1)[CH2:16][CH:2]([OH:1])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[S:12][CH:13]=[CH:14][N:15]=2)=[CH:7][CH:6]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
Reactant: NC(=O)c1cc(OCCNCc2ccccc2)ccc1O
Reactant: c1csc(-c2ccc(OCC3CO3)cc2)n1
Solvent: CC(C)O
Product: NC(=O)c1cc(OCCN(Cc2ccccc2)CC(O)COc2ccc(-c3nccs3)cc2)ccc1O

Procedure:
A solution of 6.50 g of 2-[4-(2,3-epoxypropoxy)-phenyl]-thiazole and 7.25 g of 5-[2-(benzylamino)-ethoxy]-salicylamide in 150 ml of isopropanol is heated under reflux for 18 hours and the solvent is subsequently removed in a rotary evaporator. The 1-[N-benzyl-2-(3-carbamoyl-4-hydroxyphenoxy)-ethylamino]-3-[4-(thiazol-2-yl)-phenoxy]-2-propanol, obtained in the form of an oil, is further processed in that form.
Reaction SMILES: [Cl:1][C:2]1[C:3]([F:14])=[C:4]([C:8]([CH3:13])=[C:9]([F:12])[C:10]=1[F:11])[C:5](O)=[O:6].S(Cl)([Cl:17])=O>>[Cl:1][C:2]1[C:3]([F:14])=[C:4]([C:8]([CH3:13])=[C:9]([F:12])[C:10]=1[F:11])[C:5]([Cl:17])=[O:6]
Reactant: Cc1c(F)c(F)c(Cl)c(F)c1C(=O)O
Reactant: O=S(Cl)Cl
Product: Cc1c(F)c(F)c(Cl)c(F)c1C(=O)Cl

Procedure:
Employing 3-chloro-2,4,5-trifluoro-6-methylbenzoic acid (185 mg) and thionyl chloride (600 μl ), the procedure of Reference Example 18 is repeated to give 3-chloro-2,4,5-trifluoro-6-methylbenzoyl chloride (183 mg).
Reaction SMILES: Cl.[N:2]1([CH2:7][CH:8]([N:10]2[C:23]3[CH:22]=[C:21]([C:24](Cl)=[O:25])[CH:20]=[CH:19][C:18]=3[S:17][C:16]3[C:11]2=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH3:9])[CH2:6][CH2:5][CH2:4][CH2:3]1.[N+:27]([C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32][NH2:33])([O-:29])=[O:28]>ClCCl>[N+:27]([C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32][NH:33][C:24]([C:21]1[CH:20]=[CH:19][C:18]2[S:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH:8]([CH3:9])[CH2:7][N:2]3[CH2:6][CH2:5][CH2:4][CH2:3]3)[C:23]=2[CH:22]=1)=[O:25])([O-:29])=[O:28]
Reactant: CC(CN1CCCC1)N1c2ccccc2Sc2ccc(C(=O)Cl)cc21
Reactant: NCc1ccccc1[N+](=O)[O-]
Agent: Cl
Solvent: ClCCl
Product: CC(CN1CCCC1)N1c2ccccc2Sc2ccc(C(=O)NCc3ccccc3[N+](=O)[O-])cc21
Yield: 36.9 %

Procedure:
By working in a manner similar to that described in Example 103, but starting with 10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarbonyl chloride hydrochloride (2.5 g) in dichloromethane (50 cc) and with 2-nitrobenzylamine (2.1 g), N-(2-nitrobenzyl)-10-[(2RS)-1-(1-pyrrolidinyl)-2-propyl]-2-phenothiazinecarboxamide (1.1 g) is obtained, after recrystallization in isopropyl ether, in the form of yellow crystals, m.p. 95° C.
Reaction SMILES: O=[C:2]1[CH2:8][O:7][CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.[CH3:16][NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:18]([N:17]([CH3:16])[CH:2]1[CH2:8][O:7][CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1
Reactant: CC(C)(C)OC(=O)N1CCOCC(=O)C1
Reactant: CNCc1ccccc1
Agent: CC(=O)O[BH-](OC(C)=O)OC(C)=O
Agent: [Na+]
Solvent: ClCCl
Product: CN(Cc1ccccc1)C1COCCN(C(=O)OC(C)(C)C)C1
Temperature: 25 °C
Reaction time: 0.5 h

Procedure:
A solution of tert-butyl 6-oxo-1,4-oxazepane-4-carboxylate (1.30 g (6.04 mmol) 107.1 (prepared as described in WO2004074291) in DCM (20 mL) was treated with N-methyl-benzylamine (0.857 mL, 6.64 mmol) and stirred at rt for 30 min. Sodium triacetoxyborohydride (1.54 g, 7.25 mmol) was then added, and the reaction mixture was stirred at room temperature for 24 hr. Excess hydride was quenched by the addition of H2O and the mixture was extracted with EtOAc (2×). The combined organic layers were dried with MgSO4, filtered, and concentrated in vacuo, absorbing onto 8 g SiO2. Purification by flash column chromatography (ISCO 40 g SiO2, 20% EtOAc/Hexanes then gradient to 80% EtOAc/hexanes) afforded tert-butyl 6-(benzyl(methyl)amino)-1,4-oxazepane-4-carboxylate (0.759 g) 107.2 as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ 7.35-7.28 (m, 4H), 7.27-7.19 (m, 1H), 4.19-4.10 (m, 1H), 4.06-4.03 (m, 1H), 3.99-3.95 (m, 1H), 3.87 (m, 1H), 3.77-3.75 (m, 2H), 3.64-3.56 (m, 1H), 3.50 (ddd, J=3.0, 9.9, 12.5 Hz, 1H), 3.26-3.12 (m, 2H), 3.11-2.98 (m, 1H), 2.33-2.22 (m, 3H), 1.53-1.33 (m, 9H); LCMS (ESI) m/z: 321.20 [M+H]+.
Reaction SMILES: C[O:2][C:3](=[O:39])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([Cl:22])[CH:20]=3)[N:15]([CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:14]=2[CH2:36][CH2:37][NH2:38])=[CH:6][CH:5]=1.[C:40]([C:42]1[CH:47]=[CH:46][C:45]([CH2:48][S:49](Cl)(=[O:51])=[O:50])=[CH:44][CH:43]=1)#[N:41]>>[CH:23]([N:15]1[C:16]2[C:21](=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[C:13]([CH2:12][CH2:11][O:10][C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:39])=[CH:5][CH:6]=2)=[C:14]1[CH2:36][CH2:37][NH:38][S:49]([CH2:48][C:45]1[CH:46]=[CH:47][C:42]([C:40]#[N:41])=[CH:43][CH:44]=1)(=[O:51])=[O:50])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
Reactant: N#Cc1ccc(CS(=O)(=O)Cl)cc1
Reactant: COC(=O)c1ccc(OCCc2c(CCN)n(C(c3ccccc3)c3ccccc3)c3ccc(Cl)cc23)cc1
Product: N#Cc1ccc(CS(=O)(=O)NCCc2c(CCOc3ccc(C(=O)O)cc3)c3cc(Cl)ccc3n2C(c2ccccc2)c2ccccc2)cc1

Procedure:
The title compound was prepared from 4-{2-[2-(2-amino-ethyl)-1-benzhydryl-5-chloro-1H-indol-3-yl]-ethoxy}-benzoic acid methyl ester (Step 6, Example 1)and (4-cyano-phenyl)-methanesulfonyl chloride according to Example 1 Step 7.
Reaction SMILES: [C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH3:18])=[N:15][C:16](I)=[C:10]2[CH:9]1[CH2:19][CH2:20][C:21]1[CH:26]=[C:25]([F:27])[C:24]([CH3:28])=[C:23]([F:29])[CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)[Cl:31].CO>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]2[C:14]([CH3:18])=[N:15][C:16]([Cl:31])=[C:10]2[CH:9]1[CH2:19][CH2:20][C:21]1[CH:26]=[C:25]([F:27])[C:24]([CH3:28])=[C:23]([F:29])[CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
Reactant: Cc1c(F)cc(CCC2c3c(I)nc(C)n3CCN2C(=O)OC(C)(C)C)cc1F
Reactant: ClCCl
Solvent: CO
Product: Cc1c(F)cc(CCC2c3c(Cl)nc(C)n3CCN2C(=O)OC(C)(C)C)cc1F

Procedure:
According to the general procedure (GP12), chlorination of 8-[2-(3,5-difluoro-4-methyl-phenyl)-ethyl]-1-iodo-3-methyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester (582 mg; 1.125 mmol) and purification by FC (DCM/MeOH=40/1) gave the product 1-chloro-8-[2-(3,5-difluoro-4-methyl-phenyl)-ethyl]-3-methyl-5,6-dihydro-8H-imidazo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester as a yellow oil (49 mg; 0.115 mmol). LC-MS: tR=1.02 min.; [M+H]+=426.45 g/mol.
Reaction SMILES: [F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].N1C=CC=CC=1.O[C:23]1[CH:24]=[C:25]2[C:29](=[CH:30][CH:31]=1)[N:28]([C:32](=[O:34])[CH3:33])[N:27]=[CH:26]2>ClCCl>[C:32]([N:28]1[C:29]2[C:25](=[CH:24][C:23]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])=[CH:31][CH:30]=2)[CH:26]=[N:27]1)(=[O:34])[CH3:33]
Reactant: O=S(=O)(OS(=O)(=O)C(F)(F)F)C(F)(F)F
Reactant: CC(=O)n1ncc2cc(O)ccc21
Solvent: ClCCl
Solvent: c1ccncc1
Product: CC(=O)n1ncc2cc(OS(=O)(=O)C(F)(F)F)ccc21
Temperature: 0 °C
Reaction time: 8 h
Yield: 98.6 %

Procedure:
112 μl (1.2 eq; 0.667 mmol) of trifluoromethanesulfonic anhydride and 337 μl (17.5 eq; 49.557 mmol) of pyridine, under an argon atmosphere, are added dropwise to a solution of 98 mg (1 eq; 0.556 mmol) of 1-(5-hydroxyindazol-1-yl)ethanone in 10 ml of dichloromethane on amylene, pre-cooled to 0° C. The medium is stirred and kept at 0° C. overnight under an argon atmosphere. 112 μl of trifluoromethanesulfonic anhydride and 337 μl of pyridine are added to the medium, which is stirred for 2 hours at 0° C. 112 μl of trifluoromethanesulfonic anhydride and 337 μl of pyridine are then added, and the medium is then stirred for 3 hours at 0° C. The reaction mixture is washed with 10 ml of water. The aqueous phase is treated with 2 times 10 ml of dichloromethane. The organic phase is dried over magnesium sulfate and then filtered and the solvent is evaporated off under reduced pressure in a rotary evaporator to obtain 168.9 mg of trifluoromethanesulfonic acid 1-acetyl-1H-indazol-5-yl ester are obtained.
Reaction SMILES: [C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]2[CH2:13][N:14]([C:16]3[CH:17]=[N:18][CH:19]=[C:20]([CH:24]=3)[C:21](O)=[O:22])[CH2:15][C@H:10]2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:25][C:26]1[CH:27]=[C:28]([CH:30]=[C:31]([CH3:33])[CH:32]=1)[NH2:29]>>[CH3:25][C:26]1[CH:27]=[C:28]([NH:29][C:21]([C:20]2[CH:24]=[C:16]([N:14]3[CH2:15][C@@H:10]4[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:12][C@@H:11]4[CH2:13]3)[CH:17]=[N:18][CH:19]=2)=[O:22])[CH:30]=[C:31]([CH3:33])[CH:32]=1
Reactant: CC(C)(C)OC(=O)N1C[C@@H]2CN(c3cncc(C(=O)O)c3)C[C@@H]2C1
Reactant: Cc1cc(C)cc(N)c1
Product: Cc1cc(C)cc(NC(=O)c2cncc(N3C[C@H]4CN(C(=O)OC(C)(C)C)C[C@H]4C3)c2)c1

Procedure:
The product from Example 33B and 3,5-dimethylaniline were processed as described in Example 33C to provide the title compound. MS (APCI) m/z 337 (M+H)+.