Sodium borohydride → HCID 57805586, compound

HRID 2104246Notes

Reaction equation

HRID 2104246 reaction equation
[Cl:1][C:2]1[C:3]([C:26]([F:29])([F:28])[F:27])=[N:4][N:5]([CH2:8][C:9]([N:11]2[CH2:16][CH2:15][C:14]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)([C:17]#[N:18])[CH2:13][CH2:12]2)=[O:10])[C:6]=1[CH3:7].[BH4-].[Na+]>[Co](Cl)Cl.CO>[NH2:18][CH2:17][C:14]1([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)[CH2:13][CH2:12][N:11]([C:9](=[O:10])[CH2:8][N:5]2[C:6]([CH3:7])=[C:2]([Cl:1])[C:3]([C:26]([F:27])([F:29])[F:28])=[N:4]2)[CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 16048547HCID 16048547, compound

Product 1

HCID 57805586HCID 57805586, compound

Reagents, catalysts & solvents 2

HCID 24288Cobalt(II) chlorideCatalystHCID 887MethanolSolvent

Procedure

In a 4 mL vial was added 50 mg of 1-[2-(4-chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetyl]-4-(4-chloro-phenyl)-piperidine-4-carbonitrile (0.11 mmol, 1.00 eq), 80 mg cobalt (II) chloride (0.33 mmol, 3.00 eq), 10 mg NaBH4 (0.22 mmol, 2.00 eq) and 500 uL methanol. The mixture was allowed to stir overnight at room temperature and the crude product was purified by reversed phase HPLC (acetonitrile—H2O with 0.1% TFA as the eluent) to yield 1-[4-aminomethyl-4-(4-chloro-phenyl)-piperidin-1-yl]-2-(4-chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-ethanone. MS (ES) M+H expected=448.0, found=448.1

Workup

  1. customthe crude product was purified by reversed phase HPLC (acetonitrile—H2O with 0.1% TFA as the eluent)

Sources & evidence

ORD record
ord-55c4268831524474afeb27c3e384ea29
Source dataset
uspto-grants-2009_08
Patent number
US07576218B2

Reaction notes

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