Hydrazine, dihydrochloride → HCID 178428372, compound

HRID 1828122Notes

Reaction equation

HRID 1828122 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N:19]3[C:23](=[O:24])[C:22]4[CH:25]=[C:26]([Cl:29])[CH:27]=[CH:28][C:21]=4[C:20]3=[O:30])=[C:15]([CH3:31])[CH:14]=2)=S)=O)=[CH:4][CH:3]=1.Cl.Cl.[NH2:34][NH2:35]>CN(C=O)C>[Cl:29][C:26]1[CH:27]=[CH:28][C:21]2[C:20](=[O:30])[N:19]([C:16]3[CH:17]=[CH:18][C:13]([NH:12][C:10]4[NH:9][C:7]([C:5]5[S:6][C:2]([Cl:1])=[CH:3][CH:4]=5)=[N:35][N:34]=4)=[CH:14][C:15]=3[CH3:31])[C:23](=[O:24])[C:22]=2[CH:25]=1

Participants

4

Reactant 2

HCID 17548Hydrazine, dihydrochlorideHCID 20800070(5-Chloro(2-thienyl))-n-({[4-(5-chloro-1,3-dioxobenzo[c]azolin-2-yl)-3-methylphenyl]amino}thioxomethyl)carboxamide

Product 1

HCID 178428372HCID 178428372, compoundYield 14.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of (5-chloro(2-thienyl))-N-({[4-(5-chloro-1,3-dioxobenzo[c]azolin-2-yl)-3-methylphenyl]amino}thioxomethyl)carboxamide (15 mg, 0.030 mmol) and hydrazine dihydrochloride (4 mg, 0.038 mmol) in DMF (0.3 mL) was added HgO (7 mg, 0.032 mmol). The reaction was stirred at room temp for 17 hr, and HPLC purified to give the desired product 5-chloro-2-(4-{[5-(5-chloro(2-thienyl))(4H-1,2,4-triazol-3-yl)]amino}-2-methylphenyl)benzo[c]azoline-1,3-dione (2 mg) (ES-MS (M+H)+=470, 472) and the aminoguanidine intermediate N-((1E)-2-aza-1-{[4-(5-chloro-1,3-dioxobenzo[c]azolidin-2-yl)-3-methylphenyl]amino}-2-aminovinyl)(5-chloro(2-thienyl))carboxamide (2 mg) ES-MS (M+H)+=488, 490 (2Cl).

Workup

  1. additionwas added HgO (7 mg, 0.032 mmol)
  2. customHPLC purified

Sources & evidence

ORD record
ord-74991b4db87d4c8c8615103687e4ce85
Source dataset
uspto-grants-2006_06
Patent number
US07056926B2

Reaction notes

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