Hydrazine → HCID 66858932, compound

HRID 1803246Notes

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]([N:30]1[CH:34]=[C:33]([Cl:35])[CH:32]=[N:31]1)[C:27](O)=O.[NH2:36][NH2:37]>>[Cl:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]([C:27]1[NH:37][N:36]=[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)[N:30]1[CH:34]=[C:33]([Cl:35])[CH:32]=[N:31]1

Participants

Reactant 3

HCID 9321Hydrazine

HCID 66858237HCID 66858237, compound

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

Product 1

HCID 66858932HCID 66858932, compoundYield 100%

Procedure

Methyl 4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenylcarbamimidothioate, hydroiodide (500 mg, 1.69 mmol, from preparation A) and 6-chloro-2-(4-chloro-1H-pyrazol-1-yl)hexanoic acid (423 mg, 1.685 mmol, from preparation AK) were coupled and then reacted with hydrazine (0.212 mL, 6.74 mmol) using a procedure analogous to Step A of Example 13 to afford 5-(5-chloro-1-(4-chloro-1H-pyrazol-1-yl)pentyl)-N-(4-(4-chloro-1H-imidazol-1-yl)-3-methoxyphenyl)-1H-1,2,4-triazol-3-amine (956 mg, 1.93 mmol, 100% yield). LC-MS (M+H)+ 497.2. The crude products were used in the subsequent step without purification.

Sources & evidence

ORD record: ord-8485216de9ff44d7adec8cc9c3312984
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08349880B2

Reaction notes

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