Hydrochloric Acid → HCID 178484426, compound

HRID 491812Notes

Reaction equation

HRID 491812 reaction equation
C([O:4][CH2:5][C:6]([N:8]([C@H:10]1[CH2:15][CH2:14][C@H:13]([C:16]([NH:18][C:19]2[C:23]3[CH:24]=[C:25]([C:28]([N:30]([CH3:32])[CH3:31])=[O:29])[CH:26]=[CH:27][C:22]=3[O:21][C:20]=2[C:33]([NH:35][C:36]2[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][N:37]=2)=[O:34])=[O:17])[CH2:12][CH2:11]1)[CH3:9])=[O:7])(=O)C.[OH-].[Na+].Cl>O1CCCC1.CO.C(Cl)(Cl)Cl>[CH3:31][N:30]([CH3:32])[C:28]([C:25]1[CH:26]=[CH:27][C:22]2[O:21][C:20]([C:33]([NH:35][C:36]3[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][N:37]=3)=[O:34])=[C:19]([NH:18][C:16]([C@H:13]3[CH2:14][CH2:15][C@H:10]([N:8]([C:6](=[O:7])[CH2:5][OH:4])[CH3:9])[CH2:11][CH2:12]3)=[O:17])[C:23]=2[CH:24]=1)=[O:29]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178476498HCID 178476498, compound

Product 1

HCID 178484426HCID 178484426, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Trans-3-[4-(N-acetoxyacetyl-N-methylamino)cyclohexylcarbonylamino]-5-dimethylaminocarbonyl-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (91 mg) obtained in Example 398 is dissolved in tetrahydrofuran/methanol (2:3, 5 ml), and thereto is added at room temperature 2N aqueous sodium hydroxide solution (300 μl), and the mixture is stirred for 4 hours. The reaction solution is acidified with diluted hydrochloric acid, and the mixture is diluted with chloroform. The mixture is dried over sodium sulfate, and the solvent is evaporated under reduced pressure. The resulting residue is purified by recycle HPLC to give the title compound (44 mg).

Workup

  1. dry with materialThe mixture is dried over sodium sulfate
  2. customthe solvent is evaporated under reduced pressure
  3. customThe resulting residue is purified by recycle HPLC

Sources & evidence

ORD record
ord-da4f7bb63ed741e7a9ae97020282aaf3
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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