Sodium borohydride → N-((R)-2-(3-(4-cyano-3,5-difluorophenyl)-1H-pyrazol-1-yl)propyl)-5-(1-hydroxyethyl)isoxazole-3-carboxamide

HRID 872776Notes

Reaction equation

HRID 872776 reaction equation
[C:1]([C:4]1[O:8][N:7]=[C:6]([C:9]([NH:11][CH2:12][C@H:13]([N:15]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[C:24]([F:26])[C:23]([C:27]#[N:28])=[C:22]([F:29])[CH:21]=3)=[N:16]2)[CH3:14])=[O:10])[CH:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>>[C:27]([C:23]1[C:24]([F:26])=[CH:25][C:20]([C:17]2[CH:18]=[CH:19][N:15]([C@H:13]([CH3:14])[CH2:12][NH:11][C:9]([C:6]3[CH:5]=[C:4]([CH:1]([OH:3])[CH3:2])[O:8][N:7]=3)=[O:10])[N:16]=2)=[CH:21][C:22]=1[F:29])#[N:28]

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 70656377(R)-5-acetyl-N-(2-(3-(4-cyano-3,5-difluorophenyl)-1H-pyrazol-1-yl)propyl) isoxazole-3-carboxamide

Product 1

HCID 70656198N-((R)-2-(3-(4-cyano-3,5-difluorophenyl)-1H-pyrazol-1-yl)propyl)-5-(1-hydroxyethyl)isoxazole-3-carboxamideYield 82.4%

Procedure

(R)-5-acetyl-N-(2-(3-(4-cyano-3,5-difluorophenyl)-1H-pyrazol-1-yl)propyl)isoxazole-3-carboxamide (0.047 g, 0.136 mmol) of Example 226 was reacted with sodium borohydride (0.010 g, 0.272 mmol) using the method described in Example 84. Yield of the title compound 0.045 g. 1H NMR (400 MHz; MeOD): δ 1.50 (dd, 3H), 1.59 (d, 3H), 3.75 (m, 2H), 4.93 (m, 1H), 6.53 (m, 1H), 6.79 (d, 1H), 7.67 (m, 2H), 7.73 (d, 1H).

Sources & evidence

ORD record
ord-3bdb06bef41248c3bf2f2ac5374acd78
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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