C20H17N3O3S → HCID 178432250, compound

HRID 513829Notes

Reaction equation

HRID 513829 reaction equation
Cl.Cl.[CH3:3][C:4]1[NH:8][C:7]2[CH:9]=[CH:10][C:11]([NH:13][NH2:14])=[CH:12][C:6]=2[N:5]=1.[C:15]1([S:21]([N:24]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[C:25]2[C:33]([C:35](=[CH:38]N(C)C)[C:36]#[N:37])=[O:34])(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)C>[NH2:37][C:36]1[N:13]([C:11]2[CH:10]=[CH:9][C:7]3[NH:8][C:4]([CH3:3])=[N:5][C:6]=3[CH:12]=2)[N:14]=[CH:38][C:35]=1[C:33]([C:25]1[N:24]([S:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:23])=[O:22])[C:32]2[C:27]([CH:26]=1)=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:34]

Participants

4

Reactant 2

HCID 68005415C20H17N3O3SHCID 178432278HCID 178432278, compound

Product 1

HCID 178432250HCID 178432250, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(2-Methyl-1H-benzimidazol-5-yl)-hydrazine dihydrochloride (830 mg) was added to an ethanol solution (15 ml) of crude 2-(1-benzenesulfonyl-1H-indole-2-carbonyl)-3-dimethylamino acrylonitrile (1.17 g). The reaction mixture was heated with stirring under reflux for four hours. After cooling to room temperature, the mixture was allowed to stand at room temperature. The precipitated solid was collected by filtration, and washed with ethanol to give [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-(1-benzenesulfonyl-1H-indol-2-yl)-methanone was obtained as a yellow solid (1.5 g, with a two-step yield of 91%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for four hours
  3. customto stand at room temperature
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with ethanol

Sources & evidence

ORD record
ord-20f8cec7771e43f1add9cb19dd175bc7
Source dataset
uspto-grants-2015_08
Patent number
US09102692B2

Reaction notes

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