2-(4-Fluorophenyl)pent-4-enoic acid → methyl N'-[2-(4-fluorophenyl)pent-4-enoyl]-N-[3-methoxy-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]carbamimidothioate

HRID 1803232Notes

Reaction equation

HRID 1803232 reaction equation
I.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([NH:16][C:17]([S:19][CH3:20])=[NH:18])[CH:7]=[CH:8][C:9]=1[N:10]1[CH:14]=[N:13][C:12]([CH3:15])=[N:11]1.[F:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([CH2:32][CH:33]=[CH2:34])[C:29](O)=[O:30])=[CH:24][CH:23]=1>>[F:21][C:22]1[CH:23]=[CH:24][C:25]([CH:28]([CH2:32][CH:33]=[CH2:34])[C:29]([N:18]=[C:17]([S:19][CH3:20])[NH:16][C:6]2[CH:7]=[CH:8][C:9]([N:10]3[CH:14]=[N:13][C:12]([CH3:15])=[N:11]3)=[C:4]([O:3][CH3:2])[CH:5]=2)=[O:30])=[CH:26][CH:27]=1

Participants

3

Reactant 2

HCID 183545112-(4-Fluorophenyl)pent-4-enoic acidHCID 178493238HCID 178493238, compound

Product 1

HCID 178447406methyl N'-[2-(4-fluorophenyl)pent-4-enoyl]-N-[3-methoxy-4-(3-methyl-1,2,4-triazol-1-yl)phenyl]carbamimidothioateYield 64%

Procedure

Methyl 3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydroiodide, (1.928 g, 6.95 mmol, from preparation F) and 2-(4-fluorophenyl)pent-4-enoic acid (1.62 g, 8.34 mmol, from preparation AA) were coupled using a procedure analogous to Step A of Example 1 to afford methyl N′-2-(4-fluorophenyl)pent-4-enoyl-N-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)carbamimidothioate (1.62 g, 3.57 mmol, 64% yield) as a white solid. LC-MS (M+H)+=454.2.

Sources & evidence

ORD record
ord-501075488c724ba58a44d90e80372365
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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