Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: [NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[NH:8][C:7](=[O:15])[N:6]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])[C:5]2=[O:21].C[O:23][CH:24]1[CH:28]([CH:29]=O)[CH2:27][CH:26](OC)O1>C(O)(=O)C.C(OCC)(=O)C>[CH:24]([C:28]1[CH:27]=[CH:26][N:1]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][C:11]=2[N+:12]([O-:14])=[O:13])[NH:8][C:7](=[O:15])[N:6]([NH:16][S:17]([CH3:20])(=[O:18])=[O:19])[C:5]3=[O:21])[CH:29]=1)=[O:23]
Reactant: COC1CC(C=O)C(OC)O1
Reactant: CS(=O)(=O)Nn1c(=O)[nH]c2cc([N+](=O)[O-])c(N)cc2c1=O
Solvent: CCOC(C)=O
Solvent: CC(=O)O
Product: CS(=O)(=O)Nn1c(=O)[nH]c2cc([N+](=O)[O-])c(-n3ccc(C=O)c3)cc2c1=O

Procedure:
A solution of N-(6-amino-7-nitro-2,4-dioxo-1,4-dihydro-2H-quinazolin-3-yl)-methanesulfonamide (470 mg, 1.49 mmol) and 2,5-dimethoxytetrahydrofuran-3-aldehyde (796 mg, 4.47 mmol) in acetic acid (0.5 ml) is refluxed for five hours. The solvent is removed by rotavapor evaporation to give a brown oil which is dissolved in ethyl acetate and washed three times with water. The organic layer is dried over magnesium sulfate, filtered and the solvent removed by rotavapor evaporation to give the title compound nearly pure as a brown solid, m.p. 230-245° C. (decomp).
Reaction SMILES: [CH:1]1([NH2:5])[CH2:4][CH2:3][CH2:2]1.[C:6]([O:11][CH3:12])(=[O:10])[C:7]([CH3:9])=[CH2:8]>CO>[CH3:12][O:11][C:6](=[O:10])[CH:7]([CH3:9])[CH2:8][NH:5][CH:1]1[CH2:4][CH2:3][CH2:2]1
Reactant: NC1CCC1
Reactant: C=C(C)C(=O)OC
Solvent: CO
Product: COC(=O)C(C)CNC1CCC1
Yield: 80.4 %

Procedure:
A solution of 10.72 g (0.10 mole) of cyclobutylamine, 12.01 g (0.12 mole) of methyl methacrylate and 50 mL of methanol was heated at 90 degrees for 20 hours in a pressure bottle. After cooling the mixture was concentrated, then distilled under vacuum to give 13.77 g of (rac)-3-cyclobutylamino-2-methyl-propanoic acid methyl ester as colorless oil. b.p. 70-75 degrees at 0.5 mm Hg.
Reaction SMILES: [F:1][C:2]1([F:19])[CH2:7][O:6][C:5]([NH2:8])=[N:4][C@@:3]21[C:17]1[C:12](=[CH:13][CH:14]=[C:15]([NH2:18])[CH:16]=1)[O:11][CH2:10][CH2:9]2.Cl[C:21]1[CH:22]=N[NH:24][C:25]=1[C:26]([OH:28])=O>>[NH2:8][C:5]1[O:6][CH2:7][C:2]([F:1])([F:19])[C@@:3]2([C:17]3[C:12](=[CH:13][CH:14]=[C:15]([NH:18][C:26](=[O:28])[C:25]4[CH:21]=[CH:22][C:2]([C:3]#[N:4])=[CH:7][N:24]=4)[CH:16]=3)[O:11][CH2:10][CH2:9]2)[N:4]=1
Reactant: NC1=N[C@@]2(CCOc3ccc(N)cc32)C(F)(F)CO1
Reactant: O=C(O)c1[nH]ncc1Cl
Product: N#Cc1ccc(C(=O)Nc2ccc3c(c2)[C@@]2(CCO3)N=C(N)OCC2(F)F)nc1
Yield: 34 %

Procedure:
The condensation of (R)-5′,5′-difluoro-5′,6′-dihydrospiro[chroman-4,4′-[1,3]oxazine]-2′,6-diamine (intermediate B7.1) and 4-chloro-1H-pyrazole-5-carboxylic acid yielded the title compound (34% yield) as a pale yellow solid. MS (ISP): m/z=398.1 [M+H]+.
Reaction SMILES: [CH2:1]1[C:6]2[NH:7][C:8]3[C:9]([C:14]([O:16][CH2:17]C)=[O:15])=[CH:10][CH2:11][CH2:12][C:13]=3[C:5]=2[CH:4]=[CH:3][NH:2]1.[H-].[Na+].[CH2:21](I)[CH3:22]>CN(C=O)C>[CH2:21]([CH:12]1[CH2:11][CH:10]=[C:9]([C:14]([O:16][CH3:17])=[O:15])[C:8]2[NH:7][C:6]3[CH2:1][NH:2][CH:3]=[CH:4][C:5]=3[C:13]1=2)[CH3:22]
Reactant: CCOC(=O)C1=CCCc2c1[nH]c1c2C=CNC1
Reactant: CCI
Agent: [H-]
Agent: [Na+]
Solvent: CN(C)C=O
Product: CCC1CC=C(C(=O)OC)c2[nH]c3c(c21)C=CNC3
Temperature: 0 °C
Reaction time: 0.75 h
Yield: 72.2 %

Procedure:
Ethyl 1,2,5,6-tetrahydropyrido[3,4-b]indole-8-carboxylate (0.62 g, 2.68 mmol) was dissolved in DMF (10 mL) and cooled to 0° C. Sodium hydride (60% suspension in mineral oil, 0.16 g, 6.7 mmol) was added and the mixture stirred for 45 min prior to addition of ethyl iodide (0.50 g, 3.22 mmol). The mixture was stirred for 15 hours, then quenched with water and extracted with ethyl acetate. The organic layer was then removed and the crude was redissolved in acetonitrile and then washed with hexane to remove the mineral oil. The acetonitrile layer was evaporated to afford 0.5 g of title compound.