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

HRID 1803240Notes

Reaction equation

I.[F:2][C:3]1[CH:8]=[C:7]([N:9]2[CH:13]=[N:12][C:11]([CH3:14])=[N:10]2)[C:6]([O:15][CH3:16])=[CH:5][C:4]=1[NH:17][C:18](SC)=[NH:19].[Cl:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]([C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1)[C:28](O)=O.[NH2:38][NH2:39]>>[Cl:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]([C:28]1[NH:39][N:38]=[C:18]([NH:17][C:4]2[CH:5]=[C:6]([O:15][CH3:16])[C:7]([N:9]3[CH:13]=[N:12][C:11]([CH3:14])=[N:10]3)=[CH:8][C:3]=2[F:2])[N:19]=1)[C:31]1[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=1

Participants

Reactant 3

HCID 9321Hydrazine

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

HCID 178493242HCID 178493242, compound

Product 1

HCID 668590405-(5-chloro-1-(4-fluorophenyl)pentyl)-N-(2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amineYield 12.2%

Procedure

Methyl 2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydroiodide (0.485 g, 1.642 mmol, from preparation B) and 6-chloro-2-(4-fluorophenyl)hexanoic acid (0.442 g, 1.806 mmol, from preparation AE) were coupled and then reacted with hydrazine (0.206 mL, 6.56 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-(2-fluoro-5-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine (97 mg, 0.20 mmol, 12% yield). LC-MS (M+H)+ 488.2.

Workup

customThe crude products were purified

Sources & evidence

ORD record: ord-2cb141c57a66406ea3d928c54feeca5b
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349880B2

Reaction notes

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