Water → HCID 67542813, compound

HRID 2059713Notes

Reaction equation

HRID 2059713 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[N:14]2[CH:15]=[CH:16][CH:17]=[N:18][C:13]2=[N:12][C:11]=1[C:19]1[C:27]([O:28][CH3:29])=[CH:26][C:25]([O:30][CH3:31])=[CH:24][C:20]=1[C:21]([OH:23])=O.[C:32]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])(=[O:35])[NH:33][NH2:34].O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[N:14]2[CH:15]=[CH:16][CH:17]=[N:18][C:13]2=[N:12][C:11]=1[C:19]1[C:27]([O:28][CH3:29])=[CH:26][C:25]([O:30][CH3:31])=[CH:24][C:20]=1[C:21]([NH:34][NH:33][C:32]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[O:23]

Participants

5

Reactant 3

HCID 962WaterHCID 70091tert-Butyl carbazateHCID 59509174HCID 59509174, compound

Product 1

HCID 67542813HCID 67542813, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.1 500 mg of 2-[3-(2,6-dichlorophenylamino)imidazo[1,2-a]pyrimidin-2-yl]-3,5-dimethoxybenzoic acid, 144 mg of tert-butyl carbazate and 250 mg of DAPECl are dissolved in 1 ml of DMF and stirred at RT for 16 h. The reaction mixture is poured into water, the precipitate formed is filtered off and dried. Purification by column chromatography (ethyl acetate/methanol) gives 120 mg (19%) of tert-butyl N′-{2-[3-(2,6-dichlorophenylamino)-imidazo[1,2-a]pyrimidin-2-yl]-3,5-dimethoxybenzoyl}hydrazinecarboxylate as solid; MS-FAB (M+H+)=574.2; Rf (polar method): 1.80 min.

Workup

  1. customthe precipitate formed
  2. filtrationis filtered off
  3. customdried
  4. customPurification by column chromatography (ethyl acetate/methanol)

Sources & evidence

ORD record
ord-211fc16964524994ba2cc6317fafef1e
Source dataset
uspto-grants-2012_10
Patent number
US08278312B2

Reaction notes

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