Chloroform → HCID 178507373, compound

HRID 491813Notes

Reaction equation

HRID 491813 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=3)=[O:13])=[C:9]([NH:22][C:23]([C@H:25]3[CH2:30][CH2:29][C@H:28]([N:31]4[CH2:35][CH2:34][CH2:33][C:32]4=[O:36])[CH2:27][CH2:26]3)=[O:24])[C:8]=2[CH:37]=1)([O-])=O.C(Cl)(Cl)Cl>C(O)C.O1CCCC1.[Ni]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][N:16]=3)=[O:13])=[C:9]([NH:22][C:23]([C@H:25]3[CH2:30][CH2:29][C@H:28]([N:31]4[CH2:35][CH2:34][CH2:33][C:32]4=[O:36])[CH2:27][CH2:26]3)=[O:24])[C:8]=2[CH:37]=1

Participants

5

Reactant 2

HCID 6212ChloroformHCID 178522102HCID 178522102, compound

Product 1

HCID 178507373HCID 178507373, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

Trans-5-nitro-3-[4-(2-oxopyrrolidin-1-yl)cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (2.50 g) obtained in Example 404 is suspended in ethanol/tetrahydrofuran (1:1, 400 ml), and thereto is added Raney nickel, and the mixture is stirred at room temperature under atmospheric hydrogen pressure for 12 hours. To the resulting yellow suspension is poured chloroform (200 ml), and the mixture is stirred at room temperature for 0.5 hour. The insoluble materials are removed by filtration, and the filtrate is concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: chloroform to chloroform/methanol=4/1), suspended in ethyl acetate/diethyl ether. The precipitates are collected by filtration, washed with diethyl ether, and dried to give trans-5-amino-3-[4-(2-oxopyrrolidin-1-yl)cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (1.94 g). This product (150 mg) is suspended in methanol, and the mixture is treated with 4N hydrogen chloride in dioxane to give the title compound (158 mg).

Workup

  1. stirringthe mixture is stirred at room temperature for 0.5 hour
  2. customThe insoluble materials are removed by filtration
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue is purified by silica gel column chromatography (eluent: chloroform to chloroform/methanol=4/1)
  5. filtrationThe precipitates are collected by filtration
  6. washwashed with diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-7034c190770d487781fae6483f075951
Source dataset
uspto-grants-2009_05
Patent number
US07531537B2

Reaction notes

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