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

HRID 1803243Notes

Reaction equation

HRID 1803243 reaction equation
I.[Cl:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15](SC)=[NH:16])=[CH:10][C:9]=2[O:19][CH3:20])[CH:7]=1.[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=1[F:37])[C:27](O)=O.[NH2:38][NH2:39]>>[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:27]1[NH:39][N:38]=[C:15]([NH:14][C:11]2[CH:12]=[CH:13][C:8]([N:6]3[CH:7]=[C:3]([Cl:2])[N:4]=[CH:5]3)=[C:9]([O:19][CH3:20])[CH:10]=2)[N:16]=1)[C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:31]=1[F:37]

Participants

4

Reactant 3

HCID 9321HydrazineHCID 581100876-Chloro-2-(2,4-difluorophenyl)hexanoic acidHCID 178493236methyl 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylcarbamimidothioate, hydroiodide

Product 1

HCID 668581955-(5-chloro-1-(2,4-difluorophenyl)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, hydroiodide (500 mg, 1.685 mmol, from preparation A) and 6-chloro-2-(2,4-difluorophenyl)hexanoic acid (443 mg, 1.69 mmol, from preparation AG) were coupled and then reacted with hydrazine (0.211 mL, 6.74 mmol) using a procedure analogous to Step A of Example 13. The crude product, 5-(5-chloro-1-(2,4-difluorophenyl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amine (1.03 g, 100% yield), was used in the subsequent step without purification. LC-MS (M+H)+ 507.3.

Sources & evidence

ORD record
ord-889c3da28636459992432fd08ac97333
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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