Sodium borohydride → HCID 178456032, compound

HRID 872587Notes

Reaction equation

HRID 872587 reaction equation
[C:1]([C:4]1[CH:8]=[C:7]([C:9]([NH:11][C@H:12]([CH2:28][CH3:29])[CH2:13][N:14]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([Cl:27])[CH:20]=3)=[N:15]2)=[O:10])[NH:6][N:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>>[Cl:27][C:21]1[CH:20]=[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])[CH2:28][CH3:29])[N:15]=2)[CH:24]=[CH:23][C:22]=1[C:25]#[N:26]

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 70657239(R)-3-acetyl-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)butan-2-yl)-1H-pyrazole-5-carboxamide

Product 1

HCID 178456032HCID 178456032, compoundYield 85%

Procedure

(R)-3-acetyl-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)butan-2-yl)-1H-pyrazole-5-carboxamide (225 mg, 0.55 mmol) was treated with sodium borohydride using the method of Example 102. Thus, 192 mg (85%) of title compound was obtained. 1H-NMR (400 MHz; CDCl3/MeOD): δ 1.00 (t, 3H), 1.46-1.67 (m, 5H), 4.28-4.44 (m, 3H), 4.94 (q, 1H), 7.61 (m, 2H), 7.53 (d, 1H), 7.69 (d, 1H), 7.80 (d, 1H), 8.00 (d, 1H).

Sources & evidence

ORD record
ord-f52f67957dcb40a596afc7bf90d9c8d6
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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