Hydrazine → 5-(5-chloro-1-(4-fluorophenyl)pentyl)-N-(3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine

HRID 1803279Notes

Reaction equation

I.[F:2][C:3]1[CH:4]=[C:5]([NH:15][C:16](SC)=[NH:17])[CH:6]=[CH:7][C:8]=1[N:9]1[C:13]([CH3:14])=[N:12][CH:11]=[N:10]1.[Cl:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)[C:26](O)=O.[NH2:36][NH2:37]>>[Cl:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([C:26]1[NH:37][N:36]=[C:16]([NH:15][C:5]2[CH:6]=[CH:7][C:8]([N:9]3[C:13]([CH3:14])=[N:12][CH:11]=[N:10]3)=[C:3]([F:2])[CH:4]=2)[N:17]=1)[C:29]1[CH:30]=[CH:31][C:32]([F:35])=[CH:33][CH:34]=1

Participants

Reactant 3

HCID 9321Hydrazine

HCID 581100396-Chloro-2-(4-fluorophenyl)hexanoic acid

HCID 178504012HCID 178504012, compound

Product 1

HCID 668588295-(5-chloro-1-(4-fluorophenyl)pentyl)-N-(3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amineYield 18%

Procedure

Methyl 3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydroiodide (0.739 g, 2.79 mmol, from preparation C) and 6-chloro-2-(4-fluorophenyl)hexanoic acid (0.750 g, 3.07 mmol, from preparation AE) were coupled and then reacted with hydrazine (0.350 mL, 11.2 mmol) using a procedure analogous to Step A of Example 13. The crude products were purified using silica gel chromatography (0-95% ethyl acetate/chloroform) to afford 5-(5-chloro-1-(4-fluorophenyl)pentyl)-N-(3-fluoro-4-(5-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine (230 mg, 0.502 mmol, 18% yield) as a viscous oil. LC-MS (M+H)+ 458.2.

Workup

customThe crude products were purified

Sources & evidence

ORD record: ord-53274d75cca8449fa5244965c583a42c
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349880B2

Reaction notes

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