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

HRID 1803247Notes

Reaction equation

HRID 1803247 reaction equation
I.[F:2][CH:3]([F:22])[C:4]1[N:5]=[CH:6][N:7]([C:9]2[CH:14]=[CH:13][C:12]([NH:15][C:16](SC)=[NH:17])=[CH:11][C:10]=2[O:20][CH3:21])[CH:8]=1.[Cl:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]([C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1)[C:29](O)=O.[NH2:39][NH2:40]>>[Cl:23][CH2:24][CH2:25][CH2:26][CH2:27][CH:28]([C:29]1[NH:40][N:39]=[C:16]([NH:15][C:12]2[CH:13]=[CH:14][C:9]([N:7]3[CH:8]=[C:4]([CH:3]([F:22])[F:2])[N:5]=[CH:6]3)=[C:10]([O:20][CH3:21])[CH:11]=2)[N:17]=1)[C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1

Participants

4

Reactant 3

HCID 9321HydrazineHCID 581100396-Chloro-2-(4-fluorophenyl)hexanoic acidHCID 178493234HCID 178493234, compound

Product 1

HCID 668600325-(5-chloro-1-(4-fluorophenyl)pentyl)-N-(4-(4-(difluoromethyl)-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amineYield 101.6%

Procedure

Methyl 4-(4-(difluoromethyl)-1H-imidazol-1-yl)-3-methoxyphenylcarbamimidothioate hydroiodide (500 mg, 1.601 mmol, from preparation N) and 6-chloro-2-(4-fluorophenyl)hexanoic acid (392 mg, 1.601 mmol, from preparation AH) were coupled and then reacted with hydrazine (0.201 mL, 6.40 mmol) using a procedure analogous to Step A of Example 13 to afford 5-(5-chloro-1-(4-fluorophenyl)pentyl)-N-(4-(4-(difluoromethyl)-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amine (821 mg, 100% yield). LC-MS (M+H)+ 505.3. The crude products were used in the subsequent step without purification.

Sources & evidence

ORD record
ord-60c2661cdabd45feb5f0e7229f5e6a6c
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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