Pyridine → HCID 178476483, compound

HRID 491778Notes

Reaction equation

HRID 491778 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][N:14]=3)=[O:11])=[C:7]([NH:20][C:21]([C@H:23]3[CH2:28][CH2:27][C@H:26]([N:29]([CH3:31])[CH3:30])[CH2:25][CH2:24]3)=[O:22])[C:6]=2[CH:32]=1.[C:33]([O:36][CH2:37][C:38](Cl)=[O:39])(=[O:35])[CH3:34].N1C=CC=CC=1.C(=O)([O-])O.[Na+]>ClCCl>[C:33]([O:36][CH2:37][C:38]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][N:14]=3)=[O:11])=[C:7]([NH:20][C:21]([C@H:23]3[CH2:28][CH2:27][C@H:26]([N:29]([CH3:30])[CH3:31])[CH2:25][CH2:24]3)=[O:22])[C:6]=2[CH:32]=1)=[O:39])(=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 1049PyridineHCID 26297Acetoxyacetyl chlorideHCID 516892Sodium BicarbonateHCID 178484072HCID 178484072, compound

Product 1

HCID 178476483HCID 178476483, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trans-5-amino-3-[4-(dimethylamino)cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (100 mg) obtained in Example 180 is dissolved in dichloromethane (8 ml), and thereto are added acetoxy acetylchloride (36 mg) and pyridine (36 μl) under ice-cooling, and the mixture is stirred at room temperature for 17 hours. To the reaction solution is poured a saturated aqueous sodium hydrogen carbonate solution, and the mixture is extracted with chloroform. The organic layer is washed with a saturated brine, dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: chloroform, then chloroform/methanol=50/1) to give trans-5-acetoxyacetylamino-3-[4-(dimethylamino)cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (110 mg). A portion of this product is dissolved in ethanol, and treated with 4N hydrogen chloride in ethyl acetate to give the title compound (16 mg).

Workup

  1. temperaturecooling
  2. extractionthe mixture is extracted with chloroform
  3. washThe organic layer is washed with a saturated brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated under reduced pressure
  6. customThe resulting residue is purified by NH-silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-54ba2bac7fde41c5862795f1c61d9e5c
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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