Acetyl chloride → HCID 10310336, compound

HRID 491786Notes

Reaction equation

HRID 491786 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([NH:9][C:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[O:12][C:11]=2[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=2)=[O:20])=[O:8])[CH2:3][CH2:2]1.[C:29](Cl)(=[O:31])[CH3:30].C(N(CC)CC)C>ClCCl.C(Cl)(Cl)Cl>[C:29]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]([NH:9][C:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[O:12][C:11]=2[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][N:23]=2)=[O:20])=[O:8])[CH2:3][CH2:2]1)(=[O:31])[CH3:30]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 23062699HCID 23062699, compound

Product 1

HCID 10310336HCID 10310336, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

3-[(Piperidin-4-yl)carbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (140 mg) obtained in Example 228 is suspended in dichloromethane (10 ml), and thereto are added acetyl chloride (30 μl) and triethylamine (74 μl) under ice-cooling, and the mixture is stirred at room temperature for 6 hours. The reaction solution is diluted with chloroform, washed successively with water, 5% aqueous citric acid solution, a saturated aqueous sodium hydrogen carbonate solution and a saturated brine, and dried over sodium sulfate. The solvent is evaporated under reduced pressure, and the resulting residue is dissolved in ethyl acetate, and treated with activated carbon. The resulting residue is recrystallized from ethyl acetate to give the title compound (38 mg).

Workup

  1. temperaturecooling
  2. washwashed successively with water, 5% aqueous citric acid solution
  3. dry with materiala saturated aqueous sodium hydrogen carbonate solution and a saturated brine, and dried over sodium sulfate
  4. customThe solvent is evaporated under reduced pressure
  5. dissolutionthe resulting residue is dissolved in ethyl acetate
  6. additiontreated with activated carbon
  7. customThe resulting residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-599a2a5320724364bc1f6a62bc922ec6
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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