Dimethylamine → HCID 178483160, compound

HRID 1012078Notes

Reaction equation

HRID 1012078 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].[CH3:28][NH:29][CH3:30]>C1COCC1>[CH3:28][N:29]([CH2:21][C:19]1[CH:18]=[CH:17][C:15]2[NH:16][C:12]([C:8]3[C:7]([NH:6][C:4](=[O:5])[C:3]4[C:2]([F:1])=[CH:26][CH:25]=[CH:24][C:23]=4[F:27])=[CH:11][NH:10][N:9]=3)=[N:13][C:14]=2[CH:20]=1)[CH3:30]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 178519337HCID 178519337, compound

Product 1

HCID 178483160HCID 178483160, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound was prepared in a manner analogous to Example 22B, however using 2,6-difluoro-N-[3-(5-formyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-benzamide (57.4 mg, 0.16 mmol), dry THF (5 ml), 3 Å molecular sieves, dimethylamine (35% in EtOH) (55 μL, 0.31 mmol) and triacetoxy sodium borohydride (100 mg, 0.47 mmol) to give N-[3-(5-dimethylaminomethyl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-2,6-difluoro-benzamide (11 mg, 18%) as a yellow solid. (LC/MS: Rt 2.85, [M+H]+ 397.17).

Sources & evidence

ORD record
ord-222888cbe58a47e79baf3cd500c3026f
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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