Morpholine → HCID 178479977, compound

HRID 1012067Notes

Reaction equation

HRID 1012067 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][CH:19]=[C:20](C=O)[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.[C:34](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C1COCC1>[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[N:16]([CH3:34])[C:15]3[CH:17]=[CH:18][CH:19]=[C:20]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)[C:14]=3[N:13]=2)=[N:9][NH:10][CH:11]=1)=[O:5]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 178519447HCID 178519447, compound

Product 1

HCID 178479977HCID 178479977, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,6-difluoro-N-[3-(4-formyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamide (30 mg, 0.08 mmol) and morpholine (14 mg, 0.16 mmol) in CH2Cl2 (5 ml) and THF (2 ml) was added 3 Å molecular sieves (1 g) followed by sodium triacetoxyborohydride (50 mg, 0.24 mmol) and the mixture stirred at ambient temperature under a nitrogen atmosphere for 2 h. The reaction mixture was filtered through Celite, reduced in vacuo then purified by flash column chromatography [SiO2, EtOAc-hexane (1:1, 1:0), then CH2Cl2-MeOH (95:5)] affording 2,6-difluoro-N-[3-(4-morpholin-4-yl-methyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamide (13 mg) as a cream solid. (LC/MS: Rt 1.80, [M+H]+ 439).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthen purified by flash column chromatography [SiO2, EtOAc-hexane (1:1, 1:0)

Sources & evidence

ORD record
ord-5e6e858a58dc40279d19cf473ceb0516
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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