N-methyl-2-pyrrolidone → 3-(6-tert-Butyl-4-trifluoromethyl-pyridin-3-yl)-N-(3-fluoro-4-methanesulfonylamino-benzyl)-acrylamide

HRID 2265937Notes

Reaction equation

HRID 2265937 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH2:6][NH2:7].[C:16]([C:20]1[N:25]=[CH:24][C:23]([CH:26]=[CH:27][C:28](O)=[O:29])=[C:22]([C:31]([F:34])([F:33])[F:32])[CH:21]=1)([CH3:19])([CH3:18])[CH3:17].CN1C(=O)CCC1>C1COCC1>[C:16]([C:20]1[N:25]=[CH:24][C:23]([CH:26]=[CH:27][C:28]([NH:7][CH2:6][C:5]2[CH:8]=[CH:9][C:10]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:3]([F:2])[CH:4]=2)=[O:29])=[C:22]([C:31]([F:34])([F:32])[F:33])[CH:21]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 21097525N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochlorideHCID 687849013-(6-Tert-butyl-4-trifluoromethyl-pyridin-3-yl)-acrylic acid

Product 1

HCID 687821513-(6-tert-Butyl-4-trifluoromethyl-pyridin-3-yl)-N-(3-fluoro-4-methanesulfonylamino-benzyl)-acrylamideYield 62.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Fluoro-4-methanesulfonylaminobenzylamine hydrochloride (41.2 mg, 0.162 mmol) was reacted with 3-(6-tert-butyl-4-trifluoromethyl-pyridin-3-yl)-acrylic acid (1.0 eq, 44.2 mg) DMTMM (1.0 eq, 44.8 mg) and NMP (1.2 eq, 22 μl) in THF to give the title compound (48 mg, 62.6%) after purification by column chromatography (Hex/EtOAc=1/1).

Sources & evidence

ORD record
ord-be3599f947fb4b70b75492bba890022b
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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