3-Aminoquinoline → (S)-2-Hydroxy-2-phenyl-N-quinolin-3-yl-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

HRID 1094398Notes

Reaction equation

HRID 1094398 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH2:11])[CH:2]=1.[F:12][C:13]([F:24])([F:23])[C:14]1[N:19]=[CH:18][C:17]([CH2:20][C:21]#N)=[CH:16][CH:15]=1.C([O:28][C:29](=O)[C@H:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[OH:31])(=O)C>>[OH:31][C@@H:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:29]([N:11]([C:3]1[CH:2]=[N:1][C:10]2[C:5]([CH:4]=1)=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:21][CH2:20][C:17]1[CH:18]=[N:19][C:14]([C:13]([F:24])([F:23])[F:12])=[CH:15][CH:16]=1)=[O:28]

Participants

4

Reactant 3

HCID 113753-AminoquinolineHCID 508511273-Pyridineacetonitrile, 6-(trifluoromethyl)-HCID 87431886acetyl (2S)-2-hydroxy-2-phenylacetate

Product 1

HCID 44545787(S)-2-Hydroxy-2-phenyl-N-quinolin-3-yl-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

Procedure

In analogy to example 47 (step 2) and example 48 (steps 3 & 4), Quinolin-3-ylamine, (6-Trifluoromethyl-pyridin-3-yl)-acetonitrile & (S)-(+)-O-acetyl-L-mandelic acid were successively coupled and hydrolysed to give the target compound. MS(m/e): 452.1 [M+H]+.

Workup

  1. customhydrolysed to give the target compound

Sources & evidence

ORD record
ord-8176aa8c47a64ad6bb90e8e0e73fe076
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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