Hydrazine → 5-(5-chloro-1-(6-chloropyridin-3-yl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amine

HRID 1803245Notes

Reaction equation

HRID 1803245 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:31]=[N:32][C:33]([Cl:36])=[CH:34][CH:35]=1)[C:27](O)=O.[NH2:37][NH2:38]>>[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:27]1[NH:38][N:37]=[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:31]=[N:32][C:33]([Cl:36])=[CH:34][CH:35]=1

Participants

4

Reactant 3

HCID 9321HydrazineHCID 581101616-Chloro-2-(6-chloropyridin-3-yl)hexanoic acidHCID 178493236methyl 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylcarbamimidothioate, hydroiodide

Product 1

HCID 866499265-(5-chloro-1-(6-chloropyridin-3-yl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amineYield 23%

Procedure

Methyl 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylcarbamimidothioate, hydroiodide (500 mg, 1.69 mmol, from preparation A) and 6-chloro-2-(6-chloropyridin-3-yl)hexanoic acid (442 mg, 1.69 mmol, from preparation AJ) 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 products were purified using silica gel chromatography (40-100% ethyl acetate/chloroform) to afford 5-(5-chloro-1-(6-chloropyridin-3-yl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amine (190 mg, 0.375 mmol, 23% yield) as a pink foam. LC-MS (M+H)+ 508.1.

Workup

  1. customThe crude products were purified

Sources & evidence

ORD record
ord-1b1923d3460b4a39bb27646a3255834d
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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