Allylhydrazine → 1-allyl-5-(1-(4-fluorophenyl)but-3-enyl)-N-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine

HRID 1803233Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:30][CH:31]=[CH2:32])[C:9]([N:11]=[C:12](SC)[NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH:24]=[N:23][C:22]([CH3:25])=[N:21]3)=[C:16]([O:26][CH3:27])[CH:15]=2)=O)=[CH:4][CH:3]=1.[CH2:33]([NH:36][NH2:37])[CH:34]=[CH2:35]>>[CH2:33]([N:36]1[C:9]([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[CH2:30][CH:31]=[CH2:32])=[N:11][C:12]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH:24]=[N:23][C:22]([CH3:25])=[N:21]3)=[C:16]([O:26][CH3:27])[CH:15]=2)=[N:37]1)[CH:34]=[CH2:35]

Participants

Reactant 2

HCID 81921Allylhydrazine

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

Product 1

HCID 668585511-allyl-5-(1-(4-fluorophenyl)but-3-enyl)-N-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine

Procedure

Methyl N′-2-(4-fluorophenyl)pent-4-enoyl-N-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)carbamimidothioate (0.62 g, 1.367 mmol) was reacted with allylhydrazine (70% solution in water, 0.55 mL, 5.47 mmol) using a procedure analogous to Step B of Example 1 to provide 1-allyl-5-(1-(4-fluorophenyl)but-3-enyl)-N-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine. The purified product was dissolved in 0.1% TFA/dichloromethane and reconcentrated to afford 1-allyl-5-(1-(4-fluorophenyl)but-3-enyl)-N-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine, TFA salt (446 mg, 0.692 mmol, 51% yield) as a clear solid residue. LC-MS (M+H)+=560.3.

Sources & evidence

ORD record: ord-47cf25aa5b2b4f88b6ce6de6bdb7908e
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349880B2

Reaction notes

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