1,3-Cyclohexanedione → 8-oxo-9-[5-(4,5,6-trifluoro-1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid ethyl ester

HRID 1696647Notes

Reaction equation

HRID 1696647 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[C:21]2[N:20]=[C:19]([S:22][C:23]3[O:27][C:26]([CH:28]=O)=[CH:25][CH:24]=3)[NH:18][C:17]=2[CH:16]=[C:15]([F:30])[C:14]=1[F:31].[C:32]1(=O)[CH2:37][CH2:36][CH2:35][C:34](=[O:38])[CH2:33]1>C(O)CCC>[CH2:10]([O:9][C:7]([C:3]1[NH:4][CH:5]=[C:6]2[CH:28]([C:26]3[O:27][C:23]([S:22][C:19]4[NH:18][C:17]5[CH:16]=[C:15]([F:30])[C:14]([F:31])=[C:13]([F:12])[C:21]=5[N:20]=4)=[CH:24][CH:25]=3)[C:33]3[C:34](=[O:38])[CH2:35][CH2:36][CH2:37][C:32]=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 86623879HCID 86623879, compound

Product 1

HCID 598256818-oxo-9-[5-(4,5,6-trifluoro-1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid ethyl esterYield 22.2%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A suspension of 190 mg (1.23 mmol) of 3-amino-2-ethoxycarbonylpyrrole and 367 mg (1.23 mmol) of 5-(4,5,6-trifluoro-1H-benzimidazol-2-ylsulfanyl)-furan-2-carbaldehyde (obtained from step 2) in 6.5 mL of n-butanol under argon is stirred at room temperature for 15 minutes. 1,3-Cyclohexanedione (138 mg, 1.23 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 5 mL of ethanol, cooled to 0° C. and triturated. The solid is filtered, washed with 1 mL of ethanol and 3 times with 5 mL of diisopropylether and dried under reduced pressure. 144 mg of 8-oxo-9-[5-(4,5,6-trifluoro-1H-benzimidazol-2-ylsulfanyl)-furan-2-yl]-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid ethyl ester are obtained as a yellow crystalline powder. mp: 186° C. LCMS-DAD-ELSD: 527(−): [M−H]−; 529(+): [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. filtrationThe solid is filtered
  8. washwashed with 1 mL of ethanol and 3 times with 5 mL of diisopropylether
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-2bb609cca3fd46cebe09ffb14fad179a
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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