2-Aminonicotinic acid → 2-amino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide
Reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[O:11]([C:18]1[S:22][C:21]([CH2:23][NH2:24])=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[NH2:1][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:24][CH2:23][C:21]1[S:22][C:18]([O:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:19][CH:20]=1)=[O:6]Participants
Procedure
2-Amino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide (250 mg, 0.768 mmol) obtained from 2-aminonicotinic acid and C-(5-phenoxy-thiophen-2-yl)methylamine described in Preparation Example 24 according to an analogous method to Preparation Example A+-5, and N-iodosuccinimide (190 mg, 0.845 mmol) were dissolved in tetrahydrofuran (5 mL), and the solution was stirred for 16 hours at room temperature. An aqueous solution of saturated sodium bicarbonate was added to the reaction solution at 0° C., which was then extracted with ethyl acetate, the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was evaporated in vacuo, residue was purified by NH silica gel column chromatography (hexane:ethyl acetate=1:1), and title compound (45 mg, 0.10 mmol, 13%) was obtained as a pale yellow solid.
Sources & evidence
- ORD record
- ord-e5540f853ea64e34b09f5c4e1a094638
- Source dataset
- uspto-grants-2011_04
- Patent number
- US07932272B2
Reaction notes
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