Sodium borohydride → HCID 117668009, compound

HRID 64306Notes

Reaction equation

HRID 64306 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2([C:20](OCC)=[O:21])[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)[N:5]=[C:4]([C:25]2[CH:30]=[CH:29][C:28]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:27][CH:26]=2)[C:3]=1[C:38]#[N:39].[BH4-].[Na+]>CO>[NH2:1][C:2]1[N:6]([C:7]2([CH2:20][OH:21])[CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:9][CH2:8]2)[N:5]=[C:4]([C:25]2[CH:26]=[CH:27][C:28]([O:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:29][CH:30]=2)[C:3]=1[C:38]#[N:39]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 117668210HCID 117668210, compound

Product 1

HCID 117668009HCID 117668009, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 4-(5-amino-4-cyano-3-(4-phenoxyphenyl)-1H-pyrazol-1-yl)-1-benzylpiperidine-4-carboxylate (52 mg, 0.1 mmol) in MeOH (5 mL) was added NaBH4 (8 mg, 0.2 mmol). After 10 min, the reaction was quenched with water (5 mL) and extracted with EA (10 mL×3). The organic combined layers was dried over Na2SO4 and concentrated to give the crude product (34 mg, 70.9%) as an off-white solid. MS (ESI, m/e) [M+1]+ 480.0.

Workup

  1. customthe reaction was quenched with water (5 mL)
  2. extractionextracted with EA (10 mL×3)
  3. dry with materialThe organic combined layers was dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-84685ff8f0574948b44ff727fdf00f66
Source dataset
uspto-grants-2016_09
Patent number
US09447106B2

Reaction notes

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