1,2-Dichloroethane → (3S)-N-[4-(pyrrolidinylimino)phenyl]-2N-(4-chlorophenylaminocarbonyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxamide

HRID 1432548Notes

Reaction equation

HRID 1432548 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([N:11]2[C@H:20]([C:21]([OH:23])=O)[CH2:19][C:18]3[C:13](=[CH:14][C:15]([O:26][CH3:27])=[C:16]([O:24][CH3:25])[CH:17]=3)[CH2:12]2)=[O:10])=[CH:4][CH:3]=1.[N:28]1([N:33]=[C:34]2[CH:39]=[CH:38][C:37]([NH2:40])=[CH:36][CH2:35]2)[CH2:32][CH2:31][CH2:30][CH2:29]1.C(Cl)CCl>CN(C=O)C.O>[N:28]1([N:33]=[C:34]2[CH:35]=[CH:36][C:37]([NH:40][C:21]([C@@H:20]3[CH2:19][C:18]4[C:13](=[CH:14][C:15]([O:26][CH3:27])=[C:16]([O:24][CH3:25])[CH:17]=4)[CH2:12][N:11]3[C:9]([NH:8][C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[O:10])=[O:23])=[CH:38][CH2:39]2)[CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 686963124-(Pyrrolidinylimino)phenylamineHCID 86606520(3S)-2N-(4-chlorophenylaminocarbonyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 86606521(3S)-N-[4-(pyrrolidinylimino)phenyl]-2N-(4-chlorophenylaminocarbonyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxamideYield 82.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (3S)-2N-(4-chlorophenylaminocarbonyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (100 mg, 0.26 mmol) and 4-(pyrrolidinylimino)phenylamine (97 mg, 0.51 mmol) in DMF (4 mL) and H2O (1 mL) at room temperature, EDC (196 mg, 1.02 mmol) was added. The mixture was stirred at room temperature for 2 h. It was concentrated in vacuo. The residue was purified by HPLC to give the titled compound as a powder (118 mg). MS 562.2 and 564.2 (M+H, Cl pattern).

Workup

  1. concentrationIt was concentrated in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-82b7713fe07442d7987d62d57949f4d1
Source dataset
uspto-grants-2009_11
Patent number
US07612089B2

Reaction notes

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