Ammonium Chloride → HCID 178467503, compound

HRID 872899Notes

Reaction equation

[BH4-].[Na+].[C:3]([C:6]1[C:10]([Cl:11])=[C:9]([C:12]([NH:14][C@@H:15]([CH3:31])[CH2:16][N:17]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([Cl:30])[CH:23]=3)=[N:18]2)=[O:13])[NH:8][N:7]=1)(=[O:5])[CH3:4].[Cl-].[NH4+]>C(O)C>[Cl:11][C:10]1[C:6]([CH:3]([OH:5])[CH3:4])=[N:7][NH:8][C:9]=1[C:12]([NH:14][C@@H:15]([CH3:31])[CH2:16][N:17]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([Cl:30])[CH:23]=2)=[N:18]1)=[O:13]

Participants

Conditions

Temperature: 50 °C

Procedure

Into a mixture containing sodium borohydride (0.044 g, 1.159 mmol) in ethanol (10 ml), (S)-3-acetyl-4-chloro-N-(1-(3-(3-chloro-4-cyanophenyl)-1H-pyrazol-1-yl)propan-2-yl)-1H-pyrazole-5-carboxamide (0.5 g, 1.159 mmol) of Example 314 was slowly added and the temperature was raised to 50° C. for 10 min. The reaction mixture was stirred at RT for 19 h. Saturated ammonium chloride (30 ml) was added and the mixture was extracted with ethyl acetate, combined organic layers dried with Na2SO4, filtered and evaporated. The product was purified with flash chromatography. Yield 45.6%. 1H-NMR (400 MHz; CDCl3): δ 1.24 (d, 3H), 1.58 (dd, 3H), 2.88 (bs, 1H), 4.25-4.32 (m, 1H), 4.41-4.49 (m, HA), 4.56-4.68 (m, 1H), 5.04-5.12 (m, 1H), 6.62 (d, 1H), 7.48-7.51 (m, 1H), 7.61-7.67 (m, 2H), 7.70-7.75 (m, 1H), 8.01-8.07 (m, 1H), 11.27 (bs, 1H).

Workup

additionwas slowly added
extractionthe mixture was extracted with ethyl acetate
dry with materialdried with Na2SO4
filtrationfiltered
customevaporated
customThe product was purified with flash chromatography

Sources & evidence

ORD record: ord-0a6a6f3706584b8eaa544d2204eb9e8d
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08975254B2

Reaction notes

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