N-methyl-2-pyrrolidone → 3-(6-tert-Butyl-4-trifluoromethyl-pyridin-3-yl)-N-(3-ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-acrylamide

HRID 2265938Notes

Reaction equation

HRID 2265938 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[C:8]([F:10])[C:7]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:6]([C:16]#[CH:17])[CH:5]=1.[C:18]([C:22]1[N:27]=[CH:26][C:25]([CH:28]=[CH:29][C:30](O)=[O:31])=[C:24]([C:33]([F:36])([F:35])[F:34])[CH:23]=1)([CH3:21])([CH3:20])[CH3:19].CN1C(=O)CCC1>C1COCC1>[C:18]([C:22]1[N:27]=[CH:26][C:25]([CH:28]=[CH:29][C:30]([NH:2][CH2:3][C:4]2[CH:9]=[C:8]([F:10])[C:7]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])=[C:6]([C:16]#[CH:17])[CH:5]=2)=[O:31])=[C:24]([C:33]([F:36])([F:34])[F:35])[CH:23]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 687849013-(6-Tert-butyl-4-trifluoromethyl-pyridin-3-yl)-acrylic acidHCID 866255193-Ethynyl-5-fluoro-4-methansulfonylaminobenzylamine hydrochloride

Product 1

HCID 743323883-(6-tert-Butyl-4-trifluoromethyl-pyridin-3-yl)-N-(3-ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-acrylamideYield 30.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-Aminomethyl-2-ethynyl-6-fluoro-phenyl)-methanesulfonamide HCl salt (11.2 mg, 0.04 mmol) was reacted with 3-(6-tert-butyl-4-trifluoromethyl-pyridin-3-yl)-acrylic acid (1.0 eq, 11.0 mg) DMTMM (1.0 eq, 11.1 mg) and NMP (1.2 eq, 6 μl) in THF to give the title compound (6 mg, 30.2%) after purification by column chromatography (Hex/EtOAc=3/2).

Sources & evidence

ORD record
ord-223f31e459144b88a91c51f9a718f432
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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