N-methyl-2-pyrrolidone → 3-(2-Bromo-6-tert-butyl-pyridin-3-yl)-N-(3-fluoro-4-methane sulfonylamino-benzyl)-acrylamide

HRID 2265953Notes

Reaction equation

HRID 2265953 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].[Br:16][C:17]1[C:22]([CH:23]=[CH:24][C:25](O)=[O:26])=[CH:21][CH:20]=[C:19]([C:28]([CH3:31])([CH3:30])[CH3:29])[N:18]=1.CN1C(=O)CCC1>C1COCC1>[Br:16][C:17]1[C:22]([CH:23]=[CH:24][C:25]([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:26])=[CH:21][CH:20]=[C:19]([C:28]([CH3:31])([CH3:30])[CH3:29])[N:18]=1

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 21097525N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochlorideHCID 866255233-(2-Bromo-6-tert-butyl-pyridin-3-yl)-acrylic acid

Product 1

HCID 743323903-(2-Bromo-6-tert-butyl-pyridin-3-yl)-N-(3-fluoro-4-methane sulfonylamino-benzyl)-acrylamideYield 32.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Fluoro-4-methanesulfonylaminobenzylamine hydrochloride (116 mg, 0.454 mmol) was reacted with 3-(2-bromo-6-tert-butyl-pyridin-3-yl)-acrylic acid (1.0 eq, 129 mg) DMTMM (1.0 eq, 126 mg) and NMP (1.2 eq, 60 μl) in THF to give the title compound (72 mg, 32.8%) after purification by column chromatography (Hex/EtOAc=1/1).

Sources & evidence

ORD record
ord-94a052e39cb94f4cbd96a6ec4ecfdd3b
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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