Acetyl chloride → HCID 178497418, compound

HRID 491785Notes

Reaction equation

HRID 491785 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[O:13][C:12]([C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=3)=[O:15])=[C:11]([NH:24][C:25]([C@H:27]3[CH2:32]C[C@H](NC)[CH2:29][CH2:28]3)=[O:26])[C:10]=2[CH:35]=1)=[O:5].C(Cl)(=[O:38])C.[CH2:40]([N:42]([CH2:45][CH3:46])[CH2:43][CH3:44])C.C(=O)([O-])O.[Na+]>ClCCl>[C:43]([N:42]([C@H:45]1[CH2:46][CH2:32][C@H:27]([C:25]([NH:24][C:11]2[C:10]3[CH:35]=[C:6]([C:4]([O:3][CH3:2])=[O:5])[CH:7]=[CH:8][C:9]=3[O:13][C:12]=2[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][N:18]=2)=[O:15])=[O:26])[CH2:28][CH2:29]1)[CH3:40])(=[O:38])[CH3:44]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 178484810HCID 178484810, compound

Product 1

HCID 178497418HCID 178497418, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trans-5-methoxycarbonyl-3-[4-(methylamino)cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide hydrochloride (1.50 g) obtained in Example 218 is suspended in dichloromethane (80 ml), and thereto are added acetyl chloride (307 μl) and triethylamine (1.60 ml) under ice-cooling. The mixture is warmed to room temperature, and stirred for 2 hours. To the reaction solution is poured a saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with chloroform, washed with water and a saturated brine, and dried over sodium sulfate. The solvent is evaporated under reduced pressure, and the resulting residue is purified by NH-silica gel column chromatography (eluent: chloroform) to give the title compound (1.51 g).

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with chloroform
  3. washwashed with water
  4. dry with materiala saturated brine, and dried over sodium sulfate
  5. customThe solvent is evaporated under reduced pressure
  6. customthe resulting residue is purified by NH-silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record
ord-5f9877020fc14f9a96911be12ca56b68
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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