Cyanogen Bromide → (S)-4-[2-(5-trifluoromethyl-pyridin-2-yloxy)-ethyl]-4,5-dihydro-oxazol-2-ylamine

HRID 885205Notes

Reaction equation

[NH2:1][C@@H:2]([CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][N:9]=1)[CH2:3][OH:4].[N:18]#[C:19]Br>>[F:16][C:14]([F:17])([F:15])[C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:6][CH2:5][C@H:2]2[CH2:3][O:4][C:19]([NH2:18])=[N:1]2)=[N:9][CH:10]=1

Participants

Reactant 2

HCID 10476Cyanogen Bromide

HCID 59173196(S)-2-amino-4-(5-trifluoromethyl-pyridin-2-yloxy)-butan-1-ol

Product 1

HCID 59173170(S)-4-[2-(5-trifluoromethyl-pyridin-2-yloxy)-ethyl]-4,5-dihydro-oxazol-2-ylamine

Procedure

In analogy to example 1d (S)-2-amino-4-(5-trifluoromethyl-pyridin-2-yloxy)-butan-1-ol was reacted with cyanogen bromide to give (S)-4-[2-(5-trifluoromethyl-pyridin-2-yloxy)-ethyl]-4,5-dihydro-oxazol-2-ylamine. White solid. MS (ISP): 276.2 ([M+H]+).

Sources & evidence

ORD record: ord-9fb653376347487d83fce3491d66a1aa
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08242153B2

Reaction notes

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