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Methanol → HCID 178522428, compound

HRID 1012077
Notes
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Reaction equation

HRID 1012077 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].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.CO>C1COCC1.CCOC(C)=O>[F:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:2]([F:1])[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]([CH2:21][N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:20][C:14]=3[N:13]=2)=[N:9][NH:10][CH:11]=1)=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 887MethanolHCID 8083MorpholineHCID 178519337HCID 178519337, compound

Product 1

HCID 178522428HCID 178522428, compoundYield 10.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857
Ethyl Acetate
Solvent

Procedure

To a mixture of 2,6-difluoro-N-[3-(5-formyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamide (75.0 mg, 0.20 mmol) in anhydrous THF (5 ml) stirring at ambient temperature was successively added 3 Å molecular sieves, morpholine (35 μL, 0.40 mmol) and triacetoxy sodiumborohydride (127 mg, 0.60 mmol). The mixture was stirred for 4 h, MeOH (3 ml) added and then the mixture reduced in vacuo. The residue was taken up in EtOAc, washed with water and brine, dried (MgSO4), reduced in vacuo and then purified through preparative LC/MS to give 2,6-difluoro-N-[3-(5-morpholin-4-ylmethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamide (9 mg, 10%) as a white solid. (LC/MS: Rt 1.90, [M+H]+ 439.09).

Workup

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

Sources & evidence

ORD record
ord-980750522ae74c378d86980f7321e551
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07977477B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes