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

HRID 2266000Notes

Reaction equation

HRID 2266000 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]([CH:16]=[CH2:17])[CH:5]=1.[O:18]([C:25]1[C:30]([CH:31]=[CH:32][C:33](O)=[O:34])=[CH:29][CH:28]=[C:27]([C:36]([F:39])([F:38])[F:37])[N:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=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:33](=[O:34])[CH:32]=[CH:31][C:30]1[C:25]([O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:26][C:27]([C:36]([F:37])([F:38])[F:39])=[CH:28][CH:29]=1)#[CH:17]

Participants

3

Reactant 2

HCID 687833273-(2-Phenoxy-6-trifluoromethyl-pyridin-3-yl)-acrylic acidHCID 68785944HCID 68785944, compound

Product 1

HCID 74382682N-(3-Ethynyl-5-fluoro-4-methanesulfonylamino-benzyl)-3-(2-phenoxy-6-trifluoromethyl-pyridin-3-yl)-acrylamideYield 75%

Procedure

N-(4-Aminomethyl-2-ethenyl-6-fluoro-phenyl)-methanesulfonamide HCl salt (35 mg, 0.13 mmol) was reacted with 3-(2-phenoxy-6-trifluoromethyl-pyridin-3-yl)-acrylic acid (17 mg) to give the title compound (22 mg, 75%) after purification by column chromatography (Hex/EtOAc=1/1).

Sources & evidence

ORD record
ord-eb5232b02d624dc8b7d96a09c47f7394
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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