Sodium borohydride → HCID 178466817, compound

HRID 872750Notes

Reaction equation

[C:1]([C:4]1[CH:8]=[C:7]([C:9]([NH:11][CH2:12][C@H:13]([N:15]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]#[N:27])=[C:22]([C:28]([F:31])([F:30])[F:29])[CH:21]=3)=[N:16]2)[CH3:14])=[O:10])[NH:6][N:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>>[C:26]([C:23]1[CH:24]=[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:7]3[NH:6][N:5]=[C:4]([CH:1]([OH:3])[CH3:2])[CH:8]=3)=[O:10])[N:16]=2)=[CH:21][C:22]=1[C:28]([F:31])([F:29])[F:30])#[N:27]

Participants

Reactant 2

HCID 4311764Sodium borohydride

HCID 67171710HCID 67171710, compound

Product 1

HCID 178466817HCID 178466817, compoundYield 58.8%

Procedure

(R)-3-acetyl-N-(2-(3-(4-cyano-3-(trifluoromethyl)phenyl)-1H-pyrazol-1-yl)propyl)-1H-pyrazole-5-carboxamide of Example 218 (0.1 g, 0.232 mmol) was reacted with sodium borohydride (0.018 g, 0.465 mmol) using the method of Example 84. Yield of the title compound 0.059 g. 1H NMR (400 MHz; CDCl3): δ 1.55 (d, 3H), 1.61 (d, 3H), 3.77 (m, 1H), 3.90 (m, 1H), 4.64 (m, 1H), 5.03 (q, 1H), 6.60 (s, 1H), 6.65 (d, 1H), 7.44 (bs, 1H), 7.51 (d, 1H), 7.83 (d, 1H), 8.06 (dd, 1H), 8.32 (s, 1H), 10.40 (bs, 1H).

Sources & evidence

ORD record: ord-540d19858a454cf48673166d9b894caf
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975254B2

Reaction notes

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