Methanol → HCID 178452292, compound

HRID 1012129Notes

Reaction equation

HRID 1012129 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[C:23]([F:27])[C:3]=1[C:4]([NH:6][C:7]1[C:8]([C:12]2[NH:16][C:15]3[CH:17]=[CH:18][C:19]([CH:21]=O)=[CH:20][C:14]=3[N:13]=2)=[N:9][NH:10][CH:11]=1)=[O:5].[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CO>C1COCC1.CCOC(C)=O>[C:28]([O:32][C:33]([N:35]1[CH2:40][CH2:39][N:38]([CH2:21][C:19]2[CH:18]=[CH:17][C:15]3[NH:16][C:12]([C:8]4[C:7]([NH:6][C:4](=[O:5])[C:3]5[C:2]([F:1])=[CH:26][CH:25]=[CH:24][C:23]=5[F:27])=[CH:11][NH:10][N:9]=4)=[N:13][C:14]=3[CH:20]=2)[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:29])[CH3:30]

Participants

7

Reactant 4

HCID 887MethanolHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 178519337HCID 178519337, compound

Product 1

HCID 178452292HCID 178452292, compoundYield 111.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 2,6-difluoro-N-[3-(5-formyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamide (50 mg, 0.14 mmol) in anhydrous THF (1.5 mL) stirring at ambient temperature was successively added 3 Å molecular sieves, piperazine-1-carboxylic acid tert-butyl ester (52 mg, 0.28 mmol) and sodium triacetoxy borohydride (90 mg, 0.42 mmol). The mixture was stirred for 4 h, MeOH (3 ml) added and then the mixture was reduced in vacuo. The residue was taken up in EtOAc, washed with brine, dried (MgSO4), reduced in vacuo and then purified through preparative LC/MS to give the title compound (84 mg) as a yellow oil. (LC/MS: Rt 2.22, [M+H]+ 538.15).

Workup

  1. stirringThe mixture was stirred for 4 h
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. custompurified through preparative LC/MS

Sources & evidence

ORD record
ord-456ede2e10cb401c971f402afb68b578
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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