Acetic Anhydride → N-{2-[3-(4-{[(dimethylamino)carbonyl]amino}phenyl)-4-(2-{3-[(dimethylamino)methyl]phenyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]ethyl}-N-methylacetamide

HRID 28905Notes

Reaction equation

HRID 28905 reaction equation
[CH3:1][N:2]([CH2:4][C:5]1[CH:6]=[C:7]([C:11]2[NH:40][C:14]3=[N:15][CH:16]=[CH:17][C:18]([C:19]4[C:20]([C:28]5[CH:33]=[CH:32][C:31]([NH:34][C:35](=[O:39])[N:36]([CH3:38])[CH3:37])=[CH:30][CH:29]=5)=[N:21][N:22]([CH2:24][CH2:25][NH:26][CH3:27])[CH:23]=4)=[C:13]3[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)[CH3:3].[OH-].[Na+].CC(O[C:47]([CH3:49])=[O:48])=O>CO.O>[CH3:37][N:36]([CH3:38])[C:35]([NH:34][C:31]1[CH:30]=[CH:29][C:28]([C:20]2[C:19]([C:18]3[CH:17]=[CH:16][N:15]=[C:14]4[NH:40][C:11]([C:7]5[CH:8]=[CH:9][CH:10]=[C:5]([CH2:4][N:2]([CH3:1])[CH3:3])[CH:6]=5)=[CH:12][C:13]=34)=[CH:23][N:22]([CH2:24][CH2:25][N:26]([CH3:27])[C:47](=[O:48])[CH3:49])[N:21]=2)=[CH:33][CH:32]=1)=[O:39]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium Hydroxide2×HCID 24816291HCID 24816291, compound

Product 1

HCID 58980045N-{2-[3-(4-{[(dimethylamino)carbonyl]amino}phenyl)-4-(2-{3-[(dimethylamino)methyl]phenyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-1-yl]ethyl}-N-methylacetamideYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To N′-(4-{4-(2-{3-[(dimethylamino)methyl]phenyl}-1H-pyrrolo[2,3-b]pyridin-4-yl)-1-[2-(methylamino)ethyl]-1H-pyrazol-3-yl}phenyl)-N,N-dimethylurea.3TFA (300 mg, 0.34 mMol) in MeOH (10 mL) was added with stirring at RT, aq. 1 N NaOH and Ac2O (40 uL, 0.42 mMol). After stirring for 30 min. the reaction was diluted with water, basified with aq. 1 N NaOH (0.4 mL), extracted with (9:1) CHCl3/iPrOH, dried (Na2SO4), filtered, and evaporated to dryness under vacuum. Trituration with (1:1) Et2O and petroleum ether, filtration and drying under vacuum gave the title compound (177 mg, 90%) as an off-white solid. ESMS [M+H]+: 579.7.

Workup

  1. stirringAfter stirring for 30 min. the reaction
  2. extractionextracted with (9:1) CHCl3/iPrOH
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated to dryness under vacuum
  6. filtrationTrituration with (1:1) Et2O and petroleum ether, filtration
  7. customdrying under vacuum

Sources & evidence

ORD record
ord-7f68810fbe0f4724b677b7a096bbecd7
Source dataset
uspto-grants-2008_09
Patent number
US07419988B2

Reaction notes

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