Hydrazine, ethyl-, ethanedioate (1:1) → 5-[3-(2,4-Dichlorophenyl)-1,9-dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]-1-ethyl-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 559158Notes

Reaction equation

HRID 559158 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[C:5](=O)[CH2:6][C:7]([C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[C:13]1[N:19]([CH3:32])[C:20](=[O:31])[C:21]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=3[Cl:30])=[CH:22][C:12]2=1)=O)[CH3:2].C(O)(=O)C(O)=O.[CH2:41]([NH:43][NH2:44])[CH3:42]>C(O)C>[CH2:1]([O:3][C:4]([C:5]1[CH:6]=[C:7]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH3:18])[C:13]2[N:19]([CH3:32])[C:20](=[O:31])[C:21]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=4[Cl:30])=[CH:22][C:12]3=2)[N:43]([CH2:41][CH3:42])[N:44]=1)=[O:34])[CH3:2]

Participants

4

Reactant 2

HCID 96181Hydrazine, ethyl-, ethanedioate (1:1)HCID 669974574-[3-(2,4-Dichlorophenyl)-1,9-dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]-2,4-dioxobutyric acid ethyl ester

Product 1

HCID 669980725-[3-(2,4-Dichlorophenyl)-1,9-dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]-1-ethyl-1H-pyrazole-3-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

930 mg (1.85 mmol) of compound A 4-[3-(2,4-dichlorophenyl)-1,9-dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]-2,4-dioxobutyric acid ethyl ester are dissolved in 20 ml of absolute ethanol. 583 mg (5.56 mmol) of ethylhydrazine oxalate are added and the mixture is refluxed overnight. The reaction medium is evaporated to dryness and the residue is triturated in a saturated K2CO3 solution. The product is filtered and washed with water. Purification is carried out on a silica column, elution being carried out with EtOAc.

Workup

  1. temperaturethe mixture is refluxed overnight
  2. customThe reaction medium is evaporated to dryness
  3. customthe residue is triturated in a saturated K2CO3 solution
  4. filtrationThe product is filtered
  5. washwashed with water
  6. customPurification
  7. washis carried out on a silica column, elution

Sources & evidence

ORD record
ord-cbc6c97aad13497791a1a4e340aeecef
Source dataset
uspto-grants-2011_11
Patent number
US08063061B2

Reaction notes

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