1,3-Cyclohexanedione → HCID 178470344, compound

HRID 1696644Notes

Reaction equation

HRID 1696644 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][NH:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[F:12][C:13]1[CH:14]=[CH:15][C:16]2[N:20]=[C:19]([S:21][C:22]3[O:26][C:25]([CH:27]=O)=[CH:24][CH:23]=3)[NH:18][C:17]=2[C:29]=1[F:30].[C:31]1(=O)[CH2:36][CH2:35][CH2:34][C:33](=[O:37])[CH2:32]1>C(O)CCC>[CH2:10]([O:9][C:7]([C:3]1[NH:4][CH:5]=[C:6]2[CH:27]([C:25]3[O:26][C:22]([S:21][C:19]4[NH:18][C:17]5[C:29]([F:30])=[C:13]([F:12])[CH:14]=[CH:15][C:16]=5[N:20]=4)=[CH:23][CH:24]=3)[C:32]3[C:33](=[O:37])[CH2:34][CH2:35][CH2:36][C:31]=3[NH:1][C:2]=12)=[O:8])[CH3:11]

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 2773439Ethyl 3-amino-1H-pyrrole-2-carboxylateHCID 178519730HCID 178519730, compound

Product 1

HCID 178470344HCID 178470344, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A suspension of 148.5 mg (0.96 mmol) of 3-amino-2-ethoxycarbonylpyrrole and 269.9 mg (0.96 mmol) of 5-(6,7-difluoro-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde (obtained from step 2) in 10 mL of n-butanol under argon is stirred at room temperature for 20 minutes. 1,3-Cyclohexanedione (108.0 mg, 0.96 mmol) is then added and the reaction mixture is heated at reflux temperature for 2 h. The mixture is then cooled to room temperature and concentrated under reduced pressure. The residue is taken up in ethanol, cooled to 0° C., triturated, filtered and washed 3 times with ethanol. 127 mg of 9-[5-(6,7-difluoro-1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid ethyl ester are obtained as a light-yellow crystalline powder. mp: 144-148° C. LCMS-DAD-ELSD: 509(−): [M−H]−; 511 (+): [M+H]+.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureat reflux temperature for 2 h
  3. temperatureThe mixture is then cooled to room temperature
  4. concentrationconcentrated under reduced pressure
  5. temperaturecooled to 0° C.
  6. customtriturated
  7. filtrationfiltered
  8. washwashed 3 times with ethanol

Sources & evidence

ORD record
ord-62000994fd9b4ba3802605b52b251cdc
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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