Acetone → HCID 178457038, compound

HRID 912849Notes

Reaction equation

HRID 912849 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([C:28]2[CH:35]=[CH:34][C:31]([CH2:32][NH2:33])=[CH:30][CH:29]=2)[C:6]2[NH:10][C:9]([N:11]3[CH2:16][CH2:15][N:14]([C:17]4[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:20]=[CH:19][N:18]=4)[CH2:13][CH2:12]3)=[N:8][C:7]=2[CH:27]=1.[CH3:38][C:39]([CH3:41])=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.ClCCl>[CH:39]([NH:33][CH2:32][C:31]1[CH:34]=[CH:35][C:28]([C:5]2[C:6]3[NH:10][C:9]([N:11]4[CH2:16][CH2:15][N:14]([C:17]5[C:22]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:20]=[CH:19][N:18]=5)[CH2:13][CH2:12]4)=[N:8][C:7]=3[CH:27]=[C:3]([C:2]([F:1])([F:36])[F:37])[CH:4]=2)=[CH:29][CH:30]=1)([CH3:41])[CH3:38]

Participants

7

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 178509570HCID 178509570, compound

Product 1

HCID 178457038HCID 178457038, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(5-(trifluoromethyl)-2-{4-[3-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}-1H-benzimidazol-7-yl)benzylamine (172 mg, 0.33 mmol, Example 75) and acetone (1 mL) in chloroform (5 mL) were added NaBH(OAc)3 (211 mg, 1 mmol) and one drop of acetic acid. The mixture was stirred at room temperature for 2 h, diluted with dichloromethane (30 mL), washed with satd aq. NaHCO3 solution (25 mL), dried over Na2SO4, and filtered. The filtrate was evaporated and the residue was purified by silica gel column chromatography, eluting with 5% MeOH in dichloromethane to give the title compound as white amorphous solid. MS (ESI, pos. ion) m/z: 563 (M+1), (ESI, neg. ion)

Workup

  1. washwashed with satd aq. NaHCO3 solution (25 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. customthe residue was purified by silica gel column chromatography
  6. washeluting with 5% MeOH in dichloromethane

Sources & evidence

ORD record
ord-12b7653773534037aa1593965f003fc1
Source dataset
uspto-grants-2011_09
Patent number
US08026241B2

Reaction notes

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