Ethyl bromoacetate → HCID 123682481, compound

HRID 905686Notes

Reaction equation

HRID 905686 reaction equation
CN1CCCC1=O.[CH2:8]([NH:15][C:16]1[C:21]([C:22]([NH2:24])=[O:23])=[CH:20][N:19]=[C:18]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)=[CH:28][CH:27]=2)[N:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Br[CH2:39][C:40]([O:42][CH2:43][CH3:44])=[O:41].C(=O)([O-])[O-].[K+].[K+]>O>[CH2:43]([O:42][C:40](=[O:41])[CH2:39][N:35]1[CH2:36][CH2:37][N:32]([C:29]2[CH:30]=[CH:31][C:26]([NH:25][C:18]3[N:17]=[C:16]([NH:15][CH2:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[C:21]([C:22]([NH2:24])=[O:23])=[CH:20][N:19]=3)=[CH:27][CH:28]=2)[CH2:33][CH2:34]1)[CH3:44]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 23071563HCID 23071563, compound

Product 1

HCID 123682481HCID 123682481, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 5 ml portion of 1-methyl-2-pyrrolidone solution of 400 mg of 4-benzylamino-2-[(4-piperazin-1-ylphenyl)amino]pyrimidine-5-carboxamide was mixed with 0.12 ml of ethyl bromoacetate and 200 mg of potassium carbonate, followed by stirring at room temperature for 30 minutes. The reaction mixture was mixed with water, and the organic layer was extracted with ethyl acetate-THF mixed solvent. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, and then the residue obtained by evaporating the solvent was washed with methanol to obtain ethyl[4-(4-{[5-(aminocarbonyl)-4-(benzylamino)pyrimidin-2-yl]amino}phenyl)piperazin-1-yl]acetate as a pale brown solid.

Workup

  1. extractionthe organic layer was extracted with ethyl acetate-THF mixed solvent
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe residue obtained
  5. customby evaporating the solvent
  6. washwas washed with methanol

Sources & evidence

ORD record
ord-6c3fd32658364226aaee4f1b5dfa7552
Source dataset
uspto-grants-2011_09
Patent number
US08012959B2

Reaction notes

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