Water → 2-Methylamino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

HRID 2080212Notes

Reaction equation

C(O[CH2:4][NH:5][C:6]1[N:27]=[CH:26][CH:25]=[CH:24][C:7]=1[C:8]([NH:10][CH2:11][C:12]1[S:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)=[O:9])C.[BH4-].[Na+].O>CS(C)=O>[CH3:4][NH:5][C:6]1[N:27]=[CH:26][CH:25]=[CH:24][C:7]=1[C:8]([NH:10][CH2:11][C:12]1[S:13][C:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:15][CH:16]=1)=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-(ethoxymethyl-amino)-N-(5-phenoxy-thiophene-2-ylmethyl)-nicotinamide described in Preparation Example A+-6 (148 mg, 0.385 mmol) in dimethylsulfoxide (3 mL) was added sodium borohydride (44 mg, 1.15 mmol), and the solution was stirred for 30 minutes at 100° C., followed by stirring for 20 minutes at 110° C. Furthermore, sodium borohydride (35 mg, 0.925 mmol) was added thereto, followed by stirring for 20 minutes at 110° C. Water was added to the reaction mixture, which was then extracted with ethyl acetate, the organic layer was sequentially washed with water and brine, dried over anhydrous sodium sulfate, and then, concentrated in vacuo. The obtained residue was purified by silica gel chromatography (hexane-ethyl acetate), and the title compound (86 mg, 0.26 mmol, 67%) was obtained.

Workup

stirringby stirring for 20 minutes at 110° C
stirringby stirring for 20 minutes at 110° C
extractionwas then extracted with ethyl acetate
washthe organic layer was sequentially washed with water and brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated in vacuo
customThe obtained residue was purified by silica gel chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record: ord-678f674f3e75494cb9068c34d2c9f122
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932272B2

Reaction notes

Loading…