Acetic Anhydride → HCID 57972163, compound

HRID 1799240Notes

Reaction equation

HRID 1799240 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].C(N(C(C)C)C(C)C)C.[CH:17]1([CH2:20][CH2:21][O:22][C:23]2[CH:50]=[CH:49][C:26]([C:27]([NH:29][CH:30]([CH2:37][C:38]3[CH:43]=[CH:42][C:41]([O:44][C:45]([F:48])([F:47])[F:46])=[CH:40][CH:39]=3)[C:31]([NH:33]CCO)=[O:32])=[O:28])=[CH:25][CH:24]=2)[CH2:19][CH2:18]1>C(Cl)Cl.C1COCC1>[C:5]([O:4][CH2:1][CH2:2][NH:33][C:31](=[O:32])[CH:30]([NH:29][C:27](=[O:28])[C:26]1[CH:25]=[CH:24][C:23]([O:22][CH2:21][CH2:20][CH:17]2[CH2:18][CH2:19]2)=[CH:50][CH:49]=1)[CH2:37][C:38]1[CH:43]=[CH:42][C:41]([O:44][C:45]([F:48])([F:46])[F:47])=[CH:40][CH:39]=1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 57972114HCID 57972114, compound

Product 1

HCID 57972163HCID 57972163, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

Acetic anhydride (50 μL, 0.526 mmol) and N-ethyl-N,N-diisopropylamine (84 μL, 0.479 mmol) were added to a methylene chloride:THF (1:1, V/V, 4 mL) solution of 4-(2-cyclopropylethoxy)-N-{2-[(2-hydroxyethyl)amino]-2-oxo-1-[4-(trifluoromethoxy)benzyl]ethyl}benzamide (116 mg, 0.239 mmol) prepared in Example 4. The mixture was stirred at room temperature for 65 hours. The reaction solution was evaporated, and the residue was purified by thin layer chromatography for separation (ethyl acetate, developed once) to give 65 mg of the title compound (white powder, yield: 52%).

Workup

  1. customThe reaction solution was evaporated
  2. customthe residue was purified by thin layer chromatography for separation (ethyl acetate

Sources & evidence

ORD record
ord-a5623a6462f94f1ba34e179ab77895c9
Source dataset
uspto-grants-2013_01
Patent number
US08344029B2

Reaction notes

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