Potassium Carbonate → HCID 178484074, compound

HRID 491779Notes

Reaction equation

HRID 491779 reaction equation
C([O:4][CH2:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][C:15]([C:17]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][N:21]=3)=[O:18])=[C:14]([NH:27][C:28]([C@H:30]3[CH2:35][CH2:34][C@H:33]([N:36]([CH3:38])[CH3:37])[CH2:32][CH2:31]3)=[O:29])[C:13]=2[CH:39]=1)=[O:7])(=O)C.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.CO>[ClH:26].[CH3:37][N:36]([CH3:38])[C@H:33]1[CH2:32][CH2:31][C@H:30]([C:28]([NH:27][C:14]2[C:13]3[CH:39]=[C:9]([NH:8][C:6](=[O:7])[CH2:5][OH:4])[CH:10]=[CH:11][C:12]=3[O:16][C:15]=2[C:17]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][N:21]=2)=[O:18])=[O:29])[CH2:35][CH2:34]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178476483HCID 178476483, compound

Product 1

HCID 178484074HCID 178484074, compoundYield 132.8%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Trans-5-acetoxyacetylamino-3-[4-(dimethylamino)-cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (70 mg) obtained in Example 189 is dissolved in tetrahydrofuran/methanol (1:1, 8 ml), and thereto is added potassium carbonate (5 mg), and the mixture is stirred at room temperature for 48 hours. The reaction solution is concentrated under reduced pressure, and the resulting residue is purified by silica gel column chromatography (eluent: chloroform/methanol=30/1). The resulting trans-3-[4-(dimethylamino)cyclohexylcarbonylamino]-5-hydroxyacetylamino-N-(5-chloropyridin-2-yl)-benzofuran-2-carboxamide is dissolved in ethanol, and treated with 4N hydrogen chloride in ethyl acetate to give the title compound (46 mg).

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. customthe resulting residue is purified by silica gel column chromatography (eluent: chloroform/methanol=30/1)
  3. dissolutionThe resulting trans-3-[4-(dimethylamino)cyclohexylcarbonylamino]-5-hydroxyacetylamino-N-(5-chloropyridin-2-yl)-benzofuran-2-carboxamide is dissolved in ethanol
  4. additiontreated with 4N hydrogen chloride in ethyl acetate

Sources & evidence

ORD record
ord-cc1fe93bdb3a4011ab2f124d2481674c
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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