Hydroxylamine HCl → HCID 178513598, compound

HRID 491810Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][N:15]=3)=[O:12])=[C:8]([NH:21][C:22]([C@H:24]3[CH2:29][CH2:28][C@H:27]([N:30]4[CH2:34][CH2:33][CH2:32][C:31]4=[O:35])[CH2:26][CH2:25]3)=[O:23])[C:7]=2[CH:36]=1)#[N:2].[Cl-].[OH:38][NH3+].C[O-].[Na+]>CS(C)=O.CO>[NH2:2][C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:10][C:9]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][N:15]=3)=[O:12])=[C:8]([NH:21][C:22]([C@H:24]3[CH2:25][CH2:26][C@H:27]([N:30]4[CH2:34][CH2:33][CH2:32][C:31]4=[O:35])[CH2:28][CH2:29]3)=[O:23])[C:7]=2[CH:36]=1)=[O:38]

Participants

Conditions

Temperature: 50 °C

Procedure

Trans-5-cyano-3-[4-(2-oxopyrrolidin-1-yl)cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (107 mg) obtained in Example 6 is suspended in dimethyl sulfoxide (2 ml), and thereto are added hydroxy-ammonium chloride (36 mg) and a 28% sodium methoxide in methanol (100 μl). The mixture is heated at 50° C. for 2 hours, and further at 80° C. for 2 hours. The reaction solution is poured into ice-water, and the precipitates are collected by filtration, and purified by recycle HPLC to give the title compound (25 mg; APCI-MS M/Z: 539/541 [M+H]+) and trans-5-aminocarbonyl-3-[4-(2-oxopyrrolidin-1-yl)cyclohexylcarbonylamino]-N-(5-chloropyridin-2-yl)benzofuran-2-carboxamide (18 mg; APCI-MS M/Z: 524/526 [M+H]+).

Workup

filtrationthe precipitates are collected by filtration
custompurified by recycle HPLC

Sources & evidence

ORD record: ord-c9040d411b3d439b804ee19888fb21b4
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07531537B2

Reaction notes

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