Acetic Acid → HCID 54080895, compound

HRID 2117352Notes

Reaction equation

HRID 2117352 reaction equation
[CH:1](OCC)(OCC)OCC.[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:33])[C:20]2[CH:25]=[C:24]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[CH:23]=[C:22]([F:32])[CH:21]=2)=[CH:14][C:13]=1[NH:34][C:35](=[O:50])[C:36]1[CH:41]=[C:40]([N:42]2[CH2:47][CH2:46][N:45]([CH3:48])[CH2:44][CH2:43]2)[CH:39]=[CH:38][C:37]=1[NH2:49].C(O)(=O)C>C(O)C>[F:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:33])[C:20]2[CH:25]=[C:24]([N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[CH:23]=[C:22]([F:32])[CH:21]=2)=[CH:14][C:13]=1[N:34]1[C:35](=[O:50])[C:36]2[C:37](=[CH:38][CH:39]=[C:40]([N:42]3[CH2:43][CH2:44][N:45]([CH3:48])[CH2:46][CH2:47]3)[CH:41]=2)[N:49]=[CH:1]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 31214Ethyl orthoformateHCID 22238171HCID 22238171, compound

Product 1

HCID 54080895HCID 54080895, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triethyl orthoformate (0.123 ml) was added to a stirred mixture of N-[2-fluoro-5-(3-fluoro-5-morpholinobenzamido)phenyl]-2-amino-5-(4-methylpiperazin-1-yl)benzamide (0.31 g), glacial acetic acid (0.016 ml) and ethanol (4 ml) and the resultant mixture was heated to 76° C. for 18 hours. The mixture was evaporated and the residue was partitioned between methylene chloride and a saturated aqueous solution of sodium bicarbonate. The organic solution was washed with water and with a saturated aqueous sodium chloride solution, dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol as eluent. There was thus obtained the title compound (0.119 g); NMR Spectrum: (DMSOd6) 2.23 (s, 3H), 3.22 (m, 4H), 3.72 (m, 4H), 6.99 (d, 1H), 7.12 (d, 1H), 7.29 (s, 1H), 7.47 (m, 2H), 7.63 (s, 1H), 7.89 (m, 1H), 7.97 (m, 1H), 8.18 (s, 1H), 10.44 (s, 1H); Mass Spectrum: M+H+561.

Workup

  1. customThe mixture was evaporated
  2. customthe residue was partitioned between methylene chloride
  3. washThe organic solution was washed with water and with a saturated aqueous sodium chloride solution
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica using
  7. temperatureincreasingly polar mixtures of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-b9aa81bb0f7042b8b4f0240240cccc1c
Source dataset
uspto-grants-2008_10
Patent number
US07442704B2

Reaction notes

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