(1S)-1-phenylpropan-1-amine → (S)-N-(alpha-Ethylbenzyl)-3-methyl-7-methoxy-2-phenylquinoline-4-carboxamide

HRID 2394815

Reaction equation

HRID 2394815 reaction equation
[CH3:1][C:2]1[C:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:4][C:5]2[C:10]([C:11]=1[C:12](Cl)=[O:13])=[CH:9][CH:8]=[C:7]([O:15][CH3:16])[CH:6]=2.[CH2:23]([C@H:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:24]>C(Cl)Cl.CN(C=O)C>[CH2:23]([C@H:25]([NH:32][C:12]([C:11]1[C:10]2[C:5](=[CH:6][C:7]([O:15][CH3:16])=[CH:8][CH:9]=2)[N:4]=[C:3]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:2]=1[CH3:1])=[O:13])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:24]

Participants

5

Reactant 2

HCID 6993773(1S)-1-phenylpropan-1-amineHCID 227143243-Methyl-7-methoxy-2-phenylquinoline-4-carbonylchloride

Product 1

HCID 53800998(S)-N-(alpha-Ethylbenzyl)-3-methyl-7-methoxy-2-phenylquinoline-4-carboxamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Prepared as described in Ex. 1, starting from 1.27 g (4.09 mmol) of crude 3-methyl-7-methoxy-2-phenylquinoline-4-carbonylchloride, 0.55 g (4.09 mmol) of (S)-(-)-α-ethylbenzylamine and 1.71 ml (12.27 mmol) of TEA in 24 ml of dry CH2Cl2 and 1 ml of DMF to help solubility. The reaction mixture was stirred 12 hours at room temperature.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-6a8cd2dc41ac4f62bcc83edbaf7232f5
Source dataset
uspto-grants-1998_09
Patent number
US05811553

Linked notes

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