Methoxyacetic Acid → HCID 178496381, compound

HRID 491777Notes

Reaction equation

HRID 491777 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.[CH3:33][O:34][CH2:35][C:36](O)=[O:37].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:33][O:34][CH2:35][C:36]([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:37]

Participants

7

Reactant 5

HCID 12251Methoxyacetic AcidHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178484072HCID 178484072, compound

Product 1

HCID 178496381HCID 178496381, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Trans-5-amino-3-[4-(dimethylamino)cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (100 mg) obtained in Example 180 is suspended in N,N-dimethylformamide (6 ml), and thereto are added successively methoxyacetic acid (23 mg), 1-hydroxybenzotriazole (39 mg) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (55 mg) 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, 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, then chloroform/methanol=30/1) to give trans-5-methoxyacetylamino-3-[4-(dimethylamino)cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide. Subsequently, this product is dissolved in ethanol, and treated with 4N hydrogen chloride in ethyl acetate to give the title compound (84 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-331ed56ccd724a8aaf36e9db9ae08ba9
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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