Azzindani/Open_Reaction_Data huggingface dataset:
Reaction SMILES: ClC1C=C(Cl)C=CC=1C1N=C(CC)C(N[C@H]2C3C(=CC=CC=3)C[C@@H]2O)=NC=1CC.[N+](C1C=CC(C([O:39][C@H:40]2[C@@H:44]([NH:45][C:46]3[C:51]([CH2:52][CH3:53])=[N:50][C:49]([C:54]4[CH:59]=[CH:58][C:57]([O:60][CH3:61])=[CH:56][C:55]=4[CH3:62])=[C:48]([CH2:63][CH3:64])[N:47]=3)[CH2:43][O:42][CH2:41]2)=O)=CC=1)([O-])=O>>[CH2:52]([C:51]1[C:46]([NH:45][C@H:44]2[CH2:43][O:42][CH2:41][C@H:40]2[OH:39])=[N:47][C:48]([CH2:63][CH3:64])=[C:49]([C:54]2[CH:59]=[CH:58][C:57]([O:60][CH3:61])=[CH:56][C:55]=2[CH3:62])[N:50]=1)[CH3:53]
Reactant: CCc1nc(-c2ccc(OC)cc2C)c(CC)nc1N[C@H]1COC[C@H]1OC(=O)c1ccc([N+](=O)[O-])cc1
Agent: CCc1nc(-c2ccc(Cl)cc2Cl)c(CC)nc1N[C@H]1c2ccccc2C[C@@H]1O
Product: CCc1nc(-c2ccc(OC)cc2C)c(CC)nc1N[C@H]1COC[C@H]1O

Procedure:
Following the procedure for the preparation of (1S,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol. but substituting cis-(+/−)-4-{[3,6-diethyl-5-(4-methoxy-2-methylphenyl)pyrazin-2-yl]amino}tetrahydrofuran-3-yl 4-nitrobenzoate and making non-critical variations provided the title compound as a colorless semi-solid. OAMS supporting ions at: ESI+ 358.2; MS (EI) m/z 357 (M+); HRMS (FAB) calcd for C20H27N3O3+H1 358.2130, found 358.2125.
Reaction SMILES: [CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH:3]([C:14]([OH:16])=[O:15])[NH:2]1.[OH-].[Na+].CS(C)=O.Cl.[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27]Cl.[C:30](=[S:32])=[S:31]>>[CH3:24][N:25]([CH3:29])[CH2:26][CH2:27][S:32][C:30]([N:2]1[CH:3]([C:14]([OH:16])=[O:15])[CH2:4][C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:12][C:13]=2[CH2:1]1)=[S:31]
Reactant: CN(C)CCCl
Reactant: O=C(O)C1Cc2c([nH]c3ccccc23)CN1
Reactant: S=C=S
Agent: Cl
Agent: [Na+]
Agent: [OH-]
Solvent: CS(C)=O
Product: CN(C)CCSC(=S)N1Cc2[nH]c3ccccc3c2CC1C(=O)O

Procedure:
In the same manner as described in Example 6, (3RS)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (2.16 g), 10N NaOH (2 ml), dimethylsulfoxide (6 ml), carbon disulfide (912 mg) and 2-(dimethylamino)ethyl chloride hydrochloride (1.73 g) are reacted. The precipitates are collected by filtration, washed with water and ethanol, and then dried to give the title compound (3.11 g, quantitatively) as yellow powder.