3-(2-Pyrrolidin-1-yl-6-trifluoromethyl-pyridin-3-yl)-acrylic acid → N-(3-Ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-3-(2-pyrrolidin-1-yl-6-trifluoromethyl-pyridin-3-yl)-acrylamide

HRID 2265982Notes

Reaction equation

HRID 2265982 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.[N:18]1([C:23]2[C:28]([CH:29]=[CH:30][C:31](O)=[O:32])=[CH:27][CH:26]=[C:25]([C:34]([F:37])([F:36])[F:35])[N:24]=2)[CH2:22][CH2:21][CH2:20][CH2:19]1>>[C:16]([C:6]1[CH:5]=[C:4]([CH:9]=[C:8]([F:10])[C:7]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH2:3][NH:2][C:31](=[O:32])[CH:30]=[CH:29][C:28]1[C:23]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[N:24][C:25]([C:34]([F:37])([F:35])[F:36])=[CH:26][CH:27]=1)#[CH:17]

Participants

3

Reactant 2

HCID 687840033-(2-Pyrrolidin-1-yl-6-trifluoromethyl-pyridin-3-yl)-acrylic acidHCID 866255193-Ethynyl-5-fluoro-4-methansulfonylaminobenzylamine hydrochloride

Product 1

HCID 74382535N-(3-Ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-3-(2-pyrrolidin-1-yl-6-trifluoromethyl-pyridin-3-yl)-acrylamideYield 80%

Procedure

N-(4-Aminomethyl-2-ethynyl-6-fluoro-phenyl)-methanesulfonamide HCl salt (94 mg, 0.327 mmol) was reacted with 3-(2-pyrrolidin-1-yl-6-trifluoromethyl-pyridin-3-yl)-acrylic acid (78 mg, 0.272 mmol) to give the title compound (110 mg, 80%).

Sources & evidence

ORD record
ord-9362969b37e247968cc5c3e73b851bf7
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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