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 1821221Notes

Reaction equation

HRID 1821221 reaction equation
[OH:1][C:2]([C:4](F)(F)F)=O.OC(C(F)(F)F)=O.OC(C(F)(F)F)=O.[CH3:22][N:23]([CH2:25][C:26]1[CH:27]=[C:28]([C:32]2[NH:61][C:35]3=[N:36][CH:37]=[CH:38][C:39]([C:40]4[C:41]([C:49]5[CH:54]=[CH:53][C:52]([NH:55][C:56](=[O:60])[N:57]([CH3:59])[CH3:58])=[CH:51][CH:50]=5)=[N:42][N:43]([CH2:45][CH2:46][NH:47][CH3:48])[CH:44]=4)=[C:34]3[CH:33]=2)[CH:29]=[CH:30][CH:31]=1)[CH3:24].[OH-].[Na+].CC(OC(C)=O)=O>CO.O>[CH3:58][N:57]([CH3:59])[C:56]([NH:55][C:52]1[CH:51]=[CH:50][C:49]([C:41]2[C:40]([C:39]3[CH:38]=[CH:37][N:36]=[C:35]4[NH:61][C:32]([C:28]5[CH:29]=[CH:30][CH:31]=[C:26]([CH2:25][N:23]([CH3:22])[CH3:24])[CH:27]=5)=[CH:33][C:34]=34)=[CH:44][N:43]([CH2:45][CH2:46][N:47]([CH3:48])[C:2](=[O:1])[CH3:4])[N:42]=2)=[CH:54][CH:53]=1)=[O:60]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium Hydroxide2×HCID 131727670HCID 131727670, 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-6e0a6dc1880641d681589a2b359c4a6d
Source dataset
uspto-grants-2009_10
Patent number
US07605266B2

Reaction notes

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