Sodium borohydride → HCID 178466829, compound

HRID 872755Notes

Reaction equation

HRID 872755 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([C:9]([NH:11][C@H:12]([CH3:29])[CH2:13][N:14]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[C:23]([F:25])[C:22]([C:26]#[N:27])=[C:21]([F:28])[CH:20]=3)=[N:15]2)=[O:10])[NH:6][N:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>>[C:26]([C:22]1[C:23]([F:25])=[CH:24][C:19]([C:16]2[CH:17]=[CH:18][N:14]([CH2:13][C@H:12]([NH:11][C:9]([C:7]3[NH:6][N:5]=[C:4]([CH:1]([OH:3])[CH3:2])[CH:8]=3)=[O:10])[CH3:29])[N:15]=2)=[CH:20][C:21]=1[F:28])#[N:27]

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 70655907(R)-3-acetyl-N-(1-(3-(4-cyano-3,5-difluorophenyl)-1H-pyrazol-1-yl) propan-2-yl)-1H-pyrazole-5-carboxamide

Product 1

HCID 178466829HCID 178466829, compound

Procedure

The title compound was prepared from (R)-3-acetyl-N-(1-(3-(4-cyano-3,5-difluorophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-pyrazole-5-carboxamide (90 mg, 0.226 mmol) and sodium tetrahydroborate (17 mg, 0.452 mmol) using the method of Example 84. Yield 41 mg. 1H NMR (400 MHz; CDCl3): δ 1.57 (d, 3H), 1.59 (d, 3H), 4.26 (m, 1H), 4.45 (m, 1H), 4.58 (m, 1H), 5.06 (q, 1H), 6.61 (m, 2H), 7.50 (d, 1H), 7.58 (m, 2H), 7.73 (bs, 1H), 10.44 (s, 1H).

Sources & evidence

ORD record
ord-073af7bf5c5c48f9a75335d432a083b8
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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