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

反応式

[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]

参加物

反応物 2

HCID 4311764Sodium borohydride

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

生成物 1

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

実験手順

(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).

出典と根拠

ORDレコード: ord-3bdb06bef41248c3bf2f2ac5374acd78
出典データセット: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08975254B2

反応ノート

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