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

HRID 1803252Notes

Reaction equation

HRID 1803252 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]=[C:33]([F:35])[C:32]([F:36])=[C:31]([F:37])[CH:30]=1)[C:26](O)=O.[NH2:38][NH2:39]>>[Cl:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([C:26]1[NH:39][N:38]=[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]=[C:33]([F:35])[C:32]([F:36])=[C:31]([F:37])[CH:30]=1

Participants

4

Reactant 3

HCID 9321HydrazineHCID 581100326-Chloro-2-(3,4,5-trifluorophenyl)hexanoic acidHCID 178493235HCID 178493235, compound

Product 1

HCID 668590005-(5-chloro-1-(3,4,5-trifluorophenyl)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-(3,4,5-trifluorophenyl)hexanoic acid (1.419 g, 5.05 mmol, from preparation AN) were coupled and then reacted with hydrazine (0.635 mL, 20.23 mmol) using a procedure analogous to Step A of Example 13. The crude product, 5-(5-chloro-1-(3,4,5-trifluorophenyl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amine (2.77 g, 100% yield), was used in the subsequent step without purification. LC-MS (M+H)+ 525.3.

Workup

  1. customfrom preparation AN)

Sources & evidence

ORD record
ord-ed1f6676a19742da9f806ae3a09ee913
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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