Hydrazine → HCID 66860526, compound

HRID 1803248Notes

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][CH:33]=[C:32]([F:36])[CH:31]=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:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=1

Participants

Reactant 3

HCID 9321Hydrazine

HCID 58110117HCID 58110117, compound

HCID 178493236methyl 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylcarbamimidothioate, hydroiodide

Product 1

HCID 66860526HCID 66860526, compoundYield 100%

Procedure

Methyl 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylcarbamimidothioate, hydroiodide (1.5 g, 5.05 mmol, from preparation A) and 6-chloro-2-(3-fluorophenyl)hexanoic acid (1.237 g, 5.05 mmol, from preparation AO) were coupled and then reacted with hydrazine (0.636 mL, 20.25 mmol) using a procedure analogous to Step A of Example 13. The crude product, 5-(5-chloro-1-(3-fluorophenyl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amine (2.78 g, 100% yield), was used in the subsequent step without purification. LC-MS (M+H)+ 489.2.

Sources & evidence

ORD record: ord-eb905add50824ff1a13dea3c6606bd26
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349880B2

Reaction notes

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