(R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-ol → HCID 86693345, compound

HRID 575312Notes

Reaction equation

HRID 575312 reaction equation
Br[C:2]1[C:3]([F:24])=[CH:4][C:5]2[CH:11]3[CH2:12][CH:9]([CH2:10]3)[N:8]3[C:13]([C:19]([F:22])([F:21])[F:20])=[C:14]([C:16]([NH2:18])=[O:17])[N:15]=[C:7]3[C:6]=2[CH:23]=1.[CH3:25][C:26]1[O:30][N:29]=[C:28]([C@:31]([OH:35])([C:33]#[CH:34])[CH3:32])[CH:27]=1>>[F:24][C:3]1[C:2]([C:34]#[C:33][C@@:31]([OH:35])([C:28]2[CH:27]=[C:26]([CH3:25])[O:30][N:29]=2)[CH3:32])=[CH:23][C:6]2[C:7]3[N:8]([C:13]([C:19]([F:20])([F:22])[F:21])=[C:14]([C:16]([NH2:18])=[O:17])[N:15]=3)[CH:9]3[CH2:12][CH:11]([C:5]=2[CH:4]=1)[CH2:10]3

Participants

3

Reactant 2

HCID 58221468(R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-olHCID 86693346HCID 86693346, compound

Product 1

HCID 86693345HCID 86693345, compoundYield 46%

Procedure

10-bromo-9-fluoro-3-(trifluoromethyl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide was reacted with (2R)-2-(5-methylisoxazol-3-yl)but-3-yn-2-ol via General Procedure E to afford 38 mg (46%) of (R)-9-fluoro-10-(3-hydroxy-3-(5-methylisoxazol-3-yl)but-1-yn-1-yl)-3-(trifluoromethyl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide.

Sources & evidence

ORD record
ord-a1231da6e9524ec7973056dcbea2d27f
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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