3,5-Bis(trifluoromethyl)benzaldehyde → cis-4-(3,5-Bis-trifluoromethyl-benzylamino)-2-ethyl-6-trifluoromethyl-3,4,-dihydro-2h-quinoline-1-carboxylic acid isopropyl ester

HRID 49582

Reaction equation

HRID 49582 reaction equation
[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=2)[C@H:10]([NH2:21])[CH2:9][C@@H:8]1[CH2:22][CH3:23])=[O:6])([CH3:3])[CH3:2].[F:24][C:25]([F:39])([F:38])[C:26]1[CH:27]=[C:28]([CH:31]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:33]=1)[CH:29]=O>>[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([F:18])([F:19])[F:20])=[CH:14][CH:15]=2)[C@H:10]([NH:21][CH2:29][C:28]2[CH:31]=[C:32]([C:34]([F:36])([F:37])[F:35])[CH:33]=[C:26]([C:25]([F:24])([F:38])[F:39])[CH:27]=2)[CH2:9][C@@H:8]1[CH2:22][CH3:23])=[O:6])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 1362473,5-Bis(trifluoromethyl)benzaldehydeHCID 69623683cis-4-Amino-2-ethyl-6-trifluoromethyl-3,4,-dihydro-2h-quinoline-1-carboxylic acid isopropyl ester

Product 1

HCID 131723997cis-4-(3,5-Bis-trifluoromethyl-benzylamino)-2-ethyl-6-trifluoromethyl-3,4,-dihydro-2h-quinoline-1-carboxylic acid isopropyl ester

Procedure

treating said cis-4-amino-2-ethyl-6-trifluoromethyl-3,4,-dihydro-2H-quinoline-1-carboxylic acid isopropyl ester first with 3,5-bis-trifluoromethyl-benzaldehyde under acidic conditions followed by a reducing agent to form cis-4-(3,5-bis-trifluoromethyl-benzylamino)-2-ethyl-6-trifluoromethyl-3,4,-dihydro-2H-quinoline-1-carboxylic acid isopropyl ester;

Workup

  1. additiontreating

Sources & evidence

ORD record
ord-4255667a58b641f4b7711a7a1e159ac1
Source dataset
uspto-grants-2004_03
Patent number
US06706881B2

Linked notes

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