1,3-Cyclohexanedione → HCID 178470355, compound

HRID 1696620Notes

Reaction equation

HRID 1696620 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].[C:12]([Si:16]([CH3:36])([CH3:35])[O:17][C:18]1[CH:34]=[CH:33][C:21]2[NH:22][C:23]([S:25][C:26]3[O:30][C:29]([CH:31]=O)=[CH:28][CH:27]=3)=[N:24][C:20]=2[CH:19]=1)([CH3:15])([CH3:14])[CH3:13].[C:37]1(=O)[CH2:42][CH2:41][CH2:40][C:39](=[O:43])[CH2:38]1>C(O)CCC>[CH2:10]([O:9][C:7]([C:3]1[NH:4][CH:5]=[C:6]2[CH:31]([C:29]3[O:30][C:26]([S:25][C:23]4[NH:22][C:21]5[CH:33]=[CH:34][C:18]([O:17][Si:16]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:35])[CH3:36])=[CH:19][C:20]=5[N:24]=4)=[CH:27][CH:28]=3)[C:38]3[C:39](=[O:43])[CH2:40][CH2:41][CH2:42][C:37]=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 178455022HCID 178455022, compound

Product 1

HCID 178470355HCID 178470355, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3-amino-2-ethoxycarbonyl-pyrrole (0.412 g, 2.67 mmol), 5-[5-(tert-butyl-dimethyl-silanyloxy)-1H-benzimidazol-2-ylsulfanyl]-furan-2-carbaldehyde (1.0 g, 2.67 mmol) and 1,3-cyclohexanedione (0.299 g, 2.67 mmol) in 10 ml of 1-butanol is heated at reflux temperature for 4 hours. The reaction mixture is then concentrated under reduced pressure. The residue is purified on a silica gel column (50 g) eluted successively with cyclohexane/ethyl acetate (9/1, v/v) and cyclohexane/ethyl acetate (7/3, v/v) to yield 376 mg of 9-{5-[5-(tert-butyl-dimethyl-silanyloxy)-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 as an orange solid. Yield=23%. Analytical LC/MS (method B): retention time=4.68 min., m/z=605.11 (positive ion mode).

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 4 hours
  3. concentrationThe reaction mixture is then concentrated under reduced pressure
  4. customThe residue is purified on a silica gel column (50 g)
  5. washeluted successively with cyclohexane/ethyl acetate (9/1

Sources & evidence

ORD record
ord-b3d362d6603441f79dc9a5619fda4df9
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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