Dimethylformamide → 2-Amino-N-(4-chloro-5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

HRID 2080225Notes

Reaction equation

HRID 2080225 reaction equation
[NH2:1][C:2]1[N:23]=[CH:22][CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5].CN(C)C=O.[Cl:29]N1C(=O)CCC1=O>C(#N)C.O.FC(F)(F)C(O)=O>[NH2:1][C:2]1[N:23]=[CH:22][CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:11]([Cl:29])[CH:12]=1)=[O:5]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 31398ChlorosuccinimideHCID 231304232-amino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

Product 1

HCID 231308152-Amino-N-(4-chloro-5-phenoxy-thiophen-2-ylmethyl)-nicotinamideYield 24%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolvent2×HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

To a mixture of 2-amino-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide described in Example A-67 (21 mg, 0.064 mmol) and N,N-dimethylformamide (1 mL) was added N-chlorosuccinimide (13 mg, 0.096 mmol), and the solution was stirred overnight at room temperature. The reaction solution was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), and trifluoroacetic acid salt of the title compound (7.4 mg, 0.016 mmol, 24%) was obtained.

Sources & evidence

ORD record
ord-a5740ff1020745e0a4a8418d2e244f64
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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