Water → HCID 59608077, compound

HRID 1690047Notes

Reaction equation

HRID 1690047 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]1[N:14]2[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]2=[N:12][C:11]=1[C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](O)=[O:23].[CH3:29][NH:30][C:31](=[S:34])[NH:32][NH2:33].O>CN(C=O)C>[CH3:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[C:3]=1[NH:9][C:10]1[N:14]2[CH:15]=[C:16]([F:19])[CH:17]=[CH:18][C:13]2=[N:12][C:11]=1[C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22]([NH:33][NH:32][C:31]([NH:30][CH3:29])=[S:34])=[O:23]

Participants

5

Reactant 3

HCID 962WaterHCID 2723853N-MethylhydrazinecarbothioamideHCID 59608074HCID 59608074, compound

Product 1

HCID 59608077HCID 59608077, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.1 200 mg (0.533 mmol) of 2-[3-(2,6-dimethylphenylamino)-6-fluoroimidazo[1,2-a]pyridin-2-yl]benzoic acid, 56 mg (0.533 mmol) of 4-methyl-3-thiosemicarbazide and 125 mg (0.650 mmol) of DAPECI are dissolved in 1 ml of DMF and stirred at RT for 2 hours. The mixture is subsequently added to water, the precipitated solid is filtered off with suction and dried, giving 117 mg (47%) of 1-{2-[3-(2,6-dimethylphenylamino)-6-fluoro-imidazo[1,2-a]pyridin-2-yl]benzoyl}-4-methyl-3-thiosemicarbazide as solid; MS-FAB (M+H+)=463.7; Rf (HPLC, polar method): 1.69 min. This is employed in the next step without further purification.

Workup

  1. filtrationthe precipitated solid is filtered off with suction
  2. customdried

Sources & evidence

ORD record
ord-5a426fdb97fc40549375af0b7e113315
Source dataset
uspto-grants-2012_04
Patent number
US08153649B2

Reaction notes

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