Sodium borohydride → HCID 86714652, compound

HRID 1409393Notes

Reaction equation

HRID 1409393 reaction equation
[C:1]([C:4]1[N:5]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH:6]=[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]([Cl:28])[CH:20]=3)=[N:15]2)=[O:10])[N:8]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[Cl:28][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[N:8]=[C:4]([CH:1]([OH:3])[CH3:2])[N:5]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:36])([CH3:35])[CH3:37])[CH:6]=3)=[O:10])[CH3:29])[N:15]=2)[CH:24]=[C:23]([F:25])[C:22]=1[C:26]#[N:27]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 70981912HCID 70981912, compound

Product 1

HCID 86714652HCID 86714652, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-2-Acetyl-N-(1-(3-(3-chloro-4-cyano-5-fluorophenyl)-1H-pyrazol-1-yl)-propan-2-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxamide (290 mg, 0.53 mmol) was dissolved in MeOH (20 ml). NaBH4 (30 mg, 0.79 mmol) was added to the solution in portions at 0° C. and the mixture was stirred at RT for 3 h. The reaction mixture was concentrated and dluted with water. The mixture was extracted with DCM and the organic layer was concentrated. The product was purified by column chromatography. Yield 245 mg. 1H-NMR (400 MHz; DMSO-d6): δ −0.05 (s, 9H), 0.81-0.86 (m, 2H), 1.07-1.1 (m, 3H), 1.49 (d, 3H), 3.47-3.51 (m, 2H), 4.29-4.43 (m, 3H), 4.88-4.91 (m, 1H), 5.4-5.45 (m, 3H), 7.03 (d, 1H), 7.68 (d, 1H), 7.86-8.00 (m, 4H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. extractionThe mixture was extracted with DCM
  3. concentrationthe organic layer was concentrated
  4. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-4b4415ed5fa24eefbbdb8b0342b6553f
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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