2-Methyl-1,3-benzoxazol-6-amine → (s)-2-Hydroxy-n-(2-methyl-benzooxazol-6-yl)-2-phenyl-n-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

HRID 1094401Notes

Reaction equation

HRID 1094401 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:5]=2[N:6]=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:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([CH3:1])[O:3][C:4]=2[CH:10]=1)[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 5905392-Methyl-1,3-benzoxazol-6-amineHCID 508511273-Pyridineacetonitrile, 6-(trifluoromethyl)-HCID 87431886acetyl (2S)-2-hydroxy-2-phenylacetate

Product 1

HCID 58007587(s)-2-Hydroxy-n-(2-methyl-benzooxazol-6-yl)-2-phenyl-n-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

Procedure

In analogy to example 49, 2-Methyl-benzooxazol-6-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): 456.1 [M+H]+.

Workup

  1. customhydrolysed to give the target compound

Sources & evidence

ORD record
ord-22c3ce3246e440259be49919a598d192
Source dataset
uspto-grants-2012_03
Patent number
US08133909B2

Reaction notes

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