5-Amino-2-methylpyridine → (s)-2-Hydroxy-n-(6-methyl-pyridin-3-yl)-2-phenyl-n-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

HRID 1094399Notes

Reaction equation

HRID 1094399 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([NH2:8])=[CH:4][CH:3]=1.[F:9][C:10]([F:21])([F:20])[C:11]1[N:16]=[CH:15][C:14]([CH2:17][C:18]#N)=[CH:13][CH:12]=1.C([O:25][C:26](=O)[C@H:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[OH:28])(=O)C>>[OH:28][C@@H:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:26]([N:8]([C:5]1[CH:6]=[N:7][C:2]([CH3:1])=[CH:3][CH:4]=1)[CH2:18][CH2:17][C:14]1[CH:15]=[N:16][C:11]([C:10]([F:21])([F:20])[F:9])=[CH:12][CH:13]=1)=[O:25]

Participants

4

Reactant 3

HCID 2433135-Amino-2-methylpyridineHCID 508511273-Pyridineacetonitrile, 6-(trifluoromethyl)-HCID 87431886acetyl (2S)-2-hydroxy-2-phenylacetate

Product 1

HCID 58007606(s)-2-Hydroxy-n-(6-methyl-pyridin-3-yl)-2-phenyl-n-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

Procedure

In analogy to example 49, 6-Methyl-pyridin-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): 416.1 [M+H]+.

Workup

  1. customhydrolysed to give the target compound

Sources & evidence

ORD record
ord-e3451c8264ff45a9ac23383dcf22697f
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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