Hydrazine → 5-(5-chloro-1-(2-fluorophenyl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amine

HRID 1803255Notes

Reaction equation

HRID 1803255 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14](SC)=[NH:15])=[CH:9][C:8]=2[O:18][CH3:19])[CH:6]=1.[Cl:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[F:35])[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:14]([NH:13][C:10]2[CH:11]=[CH:12][C:7]([N:5]3[CH:6]=[C:2]([Cl:1])[N:3]=[CH:4]3)=[C:8]([O:18][CH3:19])[CH:9]=2)[N:15]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[F:35]

Participants

4

Reactant 3

HCID 9321HydrazineHCID 581100566-Chloro-2-(2-fluorophenyl)hexanoic acidHCID 178493235HCID 178493235, compound

Product 1

HCID 668589545-(5-chloro-1-(2-fluorophenyl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amineYield 100%

Procedure

Methyl 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylcarbamimidothioate (1.5 g, 5.05 mmol, from preparation A) and 6-chloro-2-(2-fluorophenyl)hexanoic acid (1.24 g, 5.05 mmol, from preparation AQ) were coupled and then reacted with hydrazine (0.635 mL, 20.2 mmol) using a procedure analogous to Step A of Example 13. The crude product, 5-(5-chloro-1-(2-fluorophenyl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amine (2.68 g, 100% yield), was used in the subsequent step without purification. LC-MS (M+H)+ 489.2.

Sources & evidence

ORD record
ord-6dbb9d0f65064647bc7974a1bdbc3217
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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