Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[C:8]([C:10]2[S:11][CH:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=3)[N:14]=2)[CH:7]=[CH:6][C:5]=1Br.Cl.[N:26]1[CH:31]=[CH:30][C:29](B(O)O)=[C:28]([CH3:35])[CH:27]=1>>[Cl:22][C:17]1[CH:16]=[C:15]([C:13]2[N:14]=[C:10]([C:8]3[CH:7]=[CH:6][C:5]([C:29]4[CH:30]=[CH:31][N:26]=[CH:27][C:28]=4[CH3:35])=[C:4]([CH:9]=3)[C:3]([OH:2])=[O:24])[S:11][CH:12]=2)[CH:20]=[CH:19][C:18]=1[Cl:21]
Reactant: COC(=O)c1cc(-c2nc(-c3ccc(Cl)c(Cl)c3)cs2)ccc1Br
Reactant: Cc1cnccc1B(O)O
Agent: Cl
Product: Cc1cnccc1-c1ccc(-c2nc(-c3ccc(Cl)c(Cl)c3)cs2)cc1C(=O)O
Yield: 41.7 %

Procedure:
Using the conditions of General Procedure C for Suzuki Coupling and Hydrolysis in Parallel Mode, 2-bromo-5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-benzoic acid methyl ester (which may be prepared as described for Intermediate 6; 111 mg, 0.25 mmol) was reacted with 3-picoline-4-boronic acid hydrochloride salt (available from Combi-Blocks Inc.; 87 mg, 0.5 mmol). The resulting ester was hydrolyzed and the acid was purified to give 5-[4-(3,4-dichloro-phenyl)-thiazol-2-yl]-2-(3-methyl-pyridin-4-yl)-benzoic acid (46 mg, 42%). 1H NMR (300 MHz, DMSO-d6) δ 13.30 (br s, 1H), 8.59-8.66 (m, 2H), 8.50 (s, 1H), 8.30-8.38 (m, 2H), 8.10 (dd, J=8.5, 1.9 Hz, 1H), 7.88-7.94 (m, 1H), 7.78 (d, J=8.5 Hz, 1H), 7.56-7.63 (m, 1H), 7.52 (d, J=8.1 Hz, 1H), 2.34 (s, 3H).
Reaction SMILES: [CH:1]1([N:4](CC2C=CC(OC)=CC=2)[C:5]2[C:10]3=[N:11][CH:12]=[C:13]([C:14]#[N:15])[N:9]3[N:8]=[C:7](S(C)(=O)=O)[N:6]=2)[CH2:3][CH2:2]1.[NH2:29][C:30]1[N:35]=[C:34]([C:36]#[N:37])[CH:33]=[CH:32][CH:31]=1>>[C:36]([C:34]1[N:35]=[C:30]([NH:29][C:7]2[N:6]=[C:5]([NH:4][CH:1]3[CH2:2][CH2:3]3)[C:10]3=[N:11][CH:12]=[C:13]([C:14]#[N:15])[N:9]3[N:8]=2)[CH:31]=[CH:32][CH:33]=1)#[N:37]
Reactant: N#Cc1cccc(N)n1
Reactant: COc1ccc(CN(c2nc(S(C)(=O)=O)nn3c(C#N)cnc23)C2CC2)cc1
Product: N#Cc1cccc(Nc2nc(NC3CC3)c3ncc(C#N)n3n2)n1

Procedure:
The compound was prepared starting from 4-(cyclopropyl(4-methoxybenzyl)amino)-2-(methylsulfonyl)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (50 mg, 0.125 mmol) and 6-aminopicolinonitrile (17.94 mg, 0.151 mmol) using the procedure for Example 1E. Material was carried forward into the next step as is.
Reaction SMILES: Br[C:2]1[CH:3]=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Cl:8][C:5]1[N:4]=[CH:3][C:2]([C:13]2[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=2)=[CH:7][N:6]=1
Reactant: OB(O)c1ccc(F)cc1
Reactant: Clc1ncc(Br)cn1
Agent: O=C([O-])[O-]
Agent: [K+]
Solvent: C1COCCO1
Product: Fc1ccc(-c2cnc(Cl)nc2)cc1

Procedure:
A mixture of 5-bromo-2-chloropyrimidine (500 mg, 2 mmol), 4-fluorophenylboronic acid (430 mg, 3.1 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II)dichloromethane complex (1:1) (210 mg, 0.26 mmol) and potassium carbonate (1.8 g, 13 mmol) in 1,4-dioxane (6 mL) was irradiated under microwave at 120° C. for 30 min. After cooling, the solvent was evaporated. The residue was purified by flash chromatography eluting with ethyl acetate in hexanes to give the desired product. (376 mg) LCMS: (M+H)=209.0.
Reaction SMILES: ClC([C:7]1[CH:8]=[N:9][N:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][CH2:21][N:22]3[CH2:26][CH2:25][CH2:24][C@H:23]3[CH3:27])=[CH:14][CH:13]=2)[CH:11]=1)CCC[NH-].[H-].[Na+].[OH2:30]>O1CCCC1>[CH3:27][C@@H:23]1[CH2:24][CH2:25][CH2:26][N:22]1[CH2:21][CH2:20][CH2:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([N:10]2[CH:11]=[C:7]([N:22]3[CH2:26][CH2:25][CH2:24][C:23]3=[O:30])[CH:8]=[N:9]2)=[CH:17][CH:16]=1
Reactant: C[C@@H]1CCCN1CCCOc1ccc(-n2cc(C(Cl)CCC[NH-])cn2)cc1
Reactant: O
Agent: [H-]
Agent: [Na+]
Solvent: C1CCOC1
Product: C[C@@H]1CCCN1CCCOc1ccc(-n2cc(N3CCCC3=O)cn2)cc1
Temperature: 25 °C
Reaction time: 0.5 h

Procedure:
To a suspension of 4-chloro-N-[1-(4-{3-[(2R)-2-methylpyrrolidin-1-yl]propoxy}phenyl)-1H-pyrazol-4-yl]butylamide obtained in Example 29-(2) (0.224 g) in tetrahydrofuran (2.0 mL), sodium hydride (55% in mineral oil, 0.111 g) was added and stirred at room temperature for 30 minutes. The reaction mixture was diluted with water and extracted with chloroform. The organic layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: chloroform:methanol=100:1), and the resulting crystal was washed with diisopropyl ether to give the titled compound (0.127 g) as a light-yellow solid.
Reaction SMILES: [F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:13]([C:14]3[N:15]=[CH:16][NH:17][CH:18]=3)=[C:12]([CH3:19])[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].F[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1>>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:13]([C:14]3[N:15]=[CH:16][N:17]([C:21]4[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=4)[CH:18]=3)=[C:12]([CH3:19])[O:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]
Reactant: O=[N+]([O-])c1ccc(F)cc1
Reactant: Cc1onc(-c2ccc(F)c(F)c2)c1-c1c[nH]cn1
Product: Cc1onc(-c2ccc(F)c(F)c2)c1-c1cn(-c2ccc([N+](=O)[O-])cc2)cn1
Yield: 76 %

Procedure:
As described for Example 53, 3-(3,4-difluoro-phenyl)-4-(1H-imidazol-4-yl)-5-methyl-isoxazole (78 mg, 0.3 mmol) using 1-fluoro-4-nitrobenzene instead of 4-fluoroacetophenone was converted to the title compound (89 mg, 76%) which was obtained as a light yellow solid. MS: m/e=383.1 [M+H]+.
Reaction SMILES: [CH2:1]=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]1(S(OCCCCCCCCCCCC)(=O)=O)C=CC=C[CH:10]=1.[Na]>>[CH2:7]1[CH:8]2[CH:3]([CH2:2][CH2:1][CH2:9][CH2:10]2)[CH2:4][CH2:5][CH2:6]1
Reactant: C=Cc1ccccc1
Reactant: CCCCCCCCCCCCOS(=O)(=O)c1ccccc1
Agent: [Na]
Product: C1CCC2CCCCC2C1

Procedure:
Except for changing the amount of the styrene from 150 parts to 100 parts and not using sodium dodecyl benzenesulfonate when performing the polymerization, the same procedure was followed as in Example 6 to obtain a decalin dispersion of the polymer particles J which do not have a core-shell structure. The obtained polymer particles J had an average particle size of 500 nm. Further, except for using the obtained decalin dispersion of polymer particles J not having a core-shell structure, the same procedure was followed as in Example 1 to prepare the slurries and produce the all-solid state secondary cell and the same procedure was followed as in Example 1 to evaluate it. The results are shown in Table 1.
Reaction SMILES: [H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:11][C@H:12]([CH3:17])[C:13](OC)=[O:14])[CH2:8][CH2:9][CH3:10].O>C1COCC1>[CH2:7]([O:11][C@H:12]([CH3:17])[CH2:13][OH:14])[CH2:8][CH2:9][CH3:10]
Reactant: CCCCO[C@H](C)C(=O)OC
Agent: [Al+3]
Agent: [H-]
Agent: [Li+]
Solvent: O
Solvent: C1CCOC1
Product: CCCCO[C@H](C)CO
Yield: 65.8 %

Procedure:
THF (200 ml) was added to LiAlH4 (16.8 g), followed by agitating the mixture under ice cooling, dropwise adding thereto a solution of (R)-methyl 2-butoxypropionate (54 g) in THF (150 ml), agitating the mixture at room temperature for 3 hours, again cooling it with ice, adding water, extracting with heptane (300 ml) water-washing, concentrating and distilling the resulting concentrate under reduced pressure to obtain (R)-2-butoxy-1-propanol (29.3 g).
Reaction SMILES: [CH2:1]([O:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13](Cl)[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:19][C:20]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=1B(O)O>>[CH2:1]([O:8][C:9]1[C:14]([N+:15]([O-:17])=[O:16])=[C:13]([C:21]2[CH:22]=[CH:23][C:24]([C:26]([F:29])([F:28])[F:27])=[CH:25][C:20]=2[Cl:19])[CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
Reactant: OB(O)c1ccc(C(F)(F)F)cc1Cl
Reactant: O=[N+]([O-])c1c(Cl)ccnc1OCc1ccccc1
Product: O=[N+]([O-])c1c(-c2ccc(C(F)(F)F)cc2Cl)ccnc1OCc1ccccc1
Yield: 79 %

Procedure:
2-Benzyloxy-4-chloro-3-nitro-pyridine (Wilde, et al. WO 99/01454, which is incorporated herein by reference in its entirety) (2.0 g, 7.56 mmol) and 2-chloro-4-trifluoromethylphenylboronic acid (2.31 g, 11.3 mmol) were treated as in Part A of Example 19a to give 2.44 g (79%) of 2-benzyloxy-4-(2-chloro-4-trifluoromethyl-phenyl)-3-nitro-pyridine: MS (AP) m/z 408.8 [(M+H)+, 72].
Reaction SMILES: Cl.[F:2][CH2:3][CH2:4][CH2:5][NH2:6].Br[CH2:8][CH:9]1[O:14][C:13]2[CH:15]=[C:16]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:17]=[C:18]([F:19])[C:12]=2[CH2:11][O:10]1.FCCCN>>[F:2][CH2:3][CH2:4][CH2:5][NH:6][CH2:8][CH:9]1[O:14][C:13]2[CH:15]=[C:16]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:17]=[C:18]([F:19])[C:12]=2[CH2:11][O:10]1
Reactant: CS(=O)(=O)c1cc(F)c2c(c1)OC(CBr)OC2
Reactant: NCCCF
Agent: Cl
Product: CS(=O)(=O)c1cc(F)c2c(c1)OC(CNCCCF)OC2

Procedure:
3-Fluoropropan-1-amine HCl-salt (0.178 g, 1.52 mmol) was basified on a SCX-3 ion exchange column (TEA/MeOH). 2-(bromomethyl)-5-fluoro-7-(methylsulfonyl)-4H-1,3-benzodioxine (8.5 mg, 0.026 mmol) and 3-fluoropropan-1-amine (0.15 M in MeOH/TEA:4/1, 5 ml) was heated under microwave radiation at 120° C. for 1 h 20 min. ESIMS: m/z 322 (M+H)+.
Reaction SMILES: [CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:6]=1[N+:14]([O-])=O)[CH:2]=[CH2:3].[CH3:17]N>C(O)(C)C>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:6]=1[NH:14][CH3:17])[CH:2]=[CH2:3]
Reactant: C=CCOc1cccc([N+](=O)[O-])c1[N+](=O)[O-]
Reactant: CN
Solvent: CC(C)O
Product: C=CCOc1cccc([N+](=O)[O-])c1NC

Procedure:
A mixture of 9.0 g of 1-allyloxy-2,3-dinitrobenzene, 400 ml of isopropanol and 12.4 g of gaseous methylamine is heated, in a pressure vessel, to 90° for 3 hours, whilst stirring. After cooling and letting-down, the reaction solution is evaporated under reduced pressure. The resulting oil is dried at 50°/0.01 mm Hg for 2 hours, whereupon 1-allyloxy-2-methylamino-3-nitrobenzene is obtained; this can be used further without purification.
Reaction SMILES: [C:1]([OH:10])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[NH2:11][C@H:12]([C:18]([OH:20])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17].O>C1(C)C(C)=CC=CC=1>[C:1]([NH:17][CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]([C:18]([OH:20])=[O:19])[NH2:11])(=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]
Reactant: CCCCCCCC(=O)O
Reactant: NCCCC[C@H](N)C(=O)O
Solvent: Cc1ccccc1C
Solvent: O
Product: CCCCCCCC(=O)NCCCC[C@H](N)C(=O)O
Yield: 81.9 %

Procedure:
Lysine octanoate (35.0 g) was suspended in 300 ml of xylene using a 600-milliliter reaction vessel. The suspension was boiled through heating, and water formed through azeotropic distillation was removed outside the system. After it was identified that a stoichiometric amount of water was removed (reaction time 3 hours), the residue was cooled. Crystals precipitated were separated through filtration, and washed with 100 ml of a 50% ethanol solution. The crystals were recrystallized from a sulfuric acid aqueous solution to obtain 26.9 g of Nε -octanoyl lysine (yield 81.9%). This is designated Derivative B.