Hydrochloric Acid → HCID 178484076, compound

HRID 491780Notes

Reaction equation

HRID 491780 reaction equation
[CH3:1][N:2]([CH3:44])[CH:3]1[CH2:8][CH2:7][CH:6]([C:9]([NH:11][C:12]2[C:16]3[CH:17]=[C:18]([O:21][C@@H:22]4[CH2:27][O:26][C@@H](C5C=CC=CC=5)[O:24][CH2:23]4)[CH:19]=[CH:20][C:15]=3[O:14][C:13]=2[C:34]([NH:36][C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][N:38]=2)=[O:35])=[O:10])[CH2:5][CH2:4]1.Cl.C(=O)([O-])O.[Na+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:1][N:2]([CH3:44])[C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([NH:11][C:12]2[C:16]3[CH:17]=[C:18]([O:21][CH:22]([CH2:27][OH:26])[CH2:23][OH:24])[CH:19]=[CH:20][C:15]=3[O:14][C:13]=2[C:34]([NH:36][C:37]2[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][N:38]=2)=[O:35])=[O:10])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 178482820HCID 178482820, compound

Product 1

HCID 178484076HCID 178484076, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Trans-3-[4-(dimethylamino)cyclohexylcarbonylamino]-5-(2-phenyl-[1,3]dioxan-5-yloxy)-N-(5-chloropyridin-2-yl)-benzofuran-2-carboxamide (200 mg) obtained in Example 35 is dissolved in tetrahydrofuran (5 ml), and thereto is added 2N hydrochloric acid (5 ml), and the mixture is stirred at room temperature for 3 hours. The reaction solution is basified with a saturated aqueous sodium hydrogen carbonate solution and potassium carbonate, and 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: methanol/ethyl acetate=1/20→methanol/ethyl acetate=1/5) to give trans-3-[4-(dimethylamino)cyclohexylcarbonylamino]-5-(2-hydroxy-1-hydroxymethylethoxy)-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (162 mg). This product is dissolved in methanol, and thereto is added 4N hydrogen chloride in ethyl acetate (1 ml). The solvent is evaporated under reduced pressure, and the resulting residue is suspended in diethyl ether, and the precipitates are collected by filtration to give the title compound (141 mg).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer is washed with a saturated brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent is evaporated under reduced pressure
  5. customThe resulting residue is purified by NH-silica gel column chromatography (eluent: methanol/ethyl acetate=1/20→methanol/ethyl acetate=1/5)

Sources & evidence

ORD record
ord-7fff88077c0c4dc791e145d0ecd08fe8
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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