Water → 6-Methylamino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

HRID 2080220Notes

Reaction equation

C(O[CH2:4][NH:5][C:6]1[CH:27]=[CH:26][C:9]([C:10]([NH:12][CH2:13][C:14]2[S:15][C:16]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:17][CH:18]=2)=[O:11])=[CH:8][N:7]=1)C.[BH4-].[Na+].O.C(OCC)(=O)C>CS(C)=O>[CH3:4][NH:5][C:6]1[CH:27]=[CH:26][C:9]([C:10]([NH:12][CH2:13][C:14]2[S:15][C:16]([O:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:17][CH:18]=2)=[O:11])=[CH:8][N:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 6-(ethoxymethyl-amino)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide described in Example A-153 (427 mg, 0.92 mmol) in dimethylsulfoxide (5 mL) was added sodium borohydride (100 mg, 2.7 mmol), and the solution was stirred for 15 minutes at 100° C. Water and ethyl acetate were added to the reaction solution, which was then partitioned, and the organic layer was washed with water three times. Silica gel was added to the organic layer, the solvent was evaporated in vacuo for adsorption, and purified by silica gel column chromatography (ethyl acetate). The solvent was evaporated in vacuo, hexane, diethyl ether and ethyl acetate were added to the residue for solidification, and the title compound (150 mg, 0.44 mmol, 48.1%) was obtained as a white solid.

Workup

customwas then partitioned
washthe organic layer was washed with water three times
additionSilica gel was added to the organic layer
customthe solvent was evaporated in vacuo for adsorption
custompurified by silica gel column chromatography (ethyl acetate)
customThe solvent was evaporated in vacuo, hexane, diethyl ether and ethyl acetate
additionwere added to the residue for solidification

Sources & evidence

ORD record: ord-20a107388aeb44fa82aa02c21a050665
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932272B2

Reaction notes

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