Hydrazine → 5-(5-chloro-1-(4-(difluoromethoxy)phenyl)pentyl)-N-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine

HRID 1803298Notes

Reaction equation

HRID 1803298 reaction equation
I.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([NH:16][C:17](SC)=[NH:18])[CH:7]=[CH:8][C:9]=1[N:10]1[CH:14]=[N:13][C:12]([CH3:15])=[N:11]1.[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH:37]([F:39])[F:38])=[CH:32][CH:31]=1)[C:27](O)=O.[NH2:40][NH2:41]>>[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:27]1[NH:41][N:40]=[C:17]([NH:16][C:6]2[CH:7]=[CH:8][C:9]([N:10]3[CH:14]=[N:13][C:12]([CH3:15])=[N:11]3)=[C:4]([O:3][CH3:2])[CH:5]=2)[N:18]=1)[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH:37]([F:38])[F:39])=[CH:32][CH:31]=1

Participants

4

Reactant 3

HCID 9321HydrazineHCID 581100816-Chloro-2-(4-(difluoromethoxy)phenyl)hexanoic acidHCID 178493238HCID 178493238, compound

Product 1

HCID 668586645-(5-chloro-1-(4-(difluoromethoxy)phenyl)pentyl)-N-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine

Procedure

Methyl 3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenylcarbamimidothioate, hydroiodide (0.250 g, 0.617 mmol), from preparation F) and 6-chloro-2-(4-(difluoromethoxy)phenyl)hexanoic acid (0.271 g, 0.925 mmol, from preparation AZ) were coupled and then reacted with hydrazine (0.078 mL, 2.47 mmol) using a procedure analogous to Step A of Example 13. After an aqueous workup, 5-(5-chloro-1-(4-(difluoromethoxy)phenyl)pentyl)-N-(3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl)-1H-1,2,4-triazol-3-amine was obtained as a brown residue. The crude product was used in the next step without purification. LC-MS (M+H)+ 518.2.

Sources & evidence

ORD record
ord-4ce90b6842c1459b98761e28c8940be4
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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