Acetyl chloride → HCID 178474766, compound

HRID 491797Notes

Reaction equation

HRID 491797 reaction equation
[CH:1]([NH:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([C:11]([NH:13][C:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[O:16][C:15]=2[C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][N:27]=2)=[O:24])=[O:12])[CH2:7][CH2:6]1)([CH3:3])[CH3:2].C(N(CC)CC)C.[C:40](Cl)(=[O:42])[CH3:41].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[C:40]([N:4]([C@H:5]1[CH2:6][CH2:7][C@H:8]([C:11]([NH:13][C:14]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[O:16][C:15]=2[C:23]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][N:27]=2)=[O:24])=[O:12])[CH2:9][CH2:10]1)[CH:1]([CH3:3])[CH3:2])(=[O:42])[CH3:41]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 178457500HCID 178457500, compound

Product 1

HCID 178474766HCID 178474766, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trans-3-[4-(isopropylamino)cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (100 mg) obtained in Example 310 and triethylamine (61 μl) is dissolved in chloroform (5 ml), and thereto is added acetyl chloride (24 μl). The mixture is stirred at room temperature for one hour, and thereto is poured a saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with chloroform. The organic layer is washed successively with water and a saturated brine, dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The resulting residue is purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1, then ethyl acetate). The resulting residue is suspended in n-hexane, and collected by filtration to give the title compound (60 mg).

Workup

  1. extractionthe mixture is extracted with chloroform
  2. washThe organic layer is washed successively with water
  3. dry with materiala saturated brine, dried over sodium sulfate
  4. customthe solvent is evaporated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography (eluent
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-ad1af52fc3894e43a981899b5d8fce43
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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