1-Butanol → HCID 59825715, compound

HRID 1696667Notes

Reaction equation

HRID 1696667 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([F:33])[O:32][C:16]2=[CH:17][C:18]3[NH:22][C:21]([S:23][C:24]4[O:28][C:27](C=O)=[CH:26][CH:25]=4)=[N:20][C:19]=3[CH:31]=[C:15]2[O:14]1.[C:34]1(=[O:41])[CH2:39][CH2:38][CH2:37][C:36](=O)[CH2:35]1.[CH2:42](O)CCC>>[CH2:10]([O:9][C:7]([C:3]1[NH:4][CH:5]=[C:6]2[CH:42]([C:27]3[O:28][C:24]([S:23][C:21]4[NH:20][C:19]5[CH:31]=[C:15]6[O:14][C:13]([F:12])([F:33])[O:32][C:16]6=[CH:17][C:18]=5[N:22]=4)=[CH:25][CH:26]=3)[C:39]3[C:34](=[O:41])[CH2:35][CH2:36][CH2:37][C:38]=3[NH:1][C:2]=12)=[O:8])[CH3:11]

Participants

5

Reactant 4

HCID 2631-ButanolHCID 104341,3-CyclohexanedioneHCID 2773439Ethyl 3-amino-1H-pyrrole-2-carboxylateHCID 86623885HCID 86623885, compound

Product 1

HCID 59825715HCID 59825715, compoundYield 6%

Procedure

A mixture of 3-amino-2-ethoxycarbonyl-pyrrole (0.095 g, 0.62 mmol), 5-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-ylsulfanyl)-furan-2-carbaldehyde (0.20 g, 0.62 mmol) and 1,3-cyclohexanedione (0.069 g, 0.62 mmol) in 10 ml of 1-butanol is heated at reflux temperature for 4 h. The reaction mixture is then concentrated under reduced pressure and the residue is purified on a silica gel column (34 g) eluted with a mixture of cyclohexane and ethyl acetate (7/3, v/v). The fractions containing the expected product are concentrated under reduced pressure. The residue is resuspended in 2 ml of acetonitrile, heated at reflux temperature for 30 minutes and let to cool to room temperature. The insoluble material is collected by filtration and dried under vacuum to yield 19 mg of 9-[5-(2,2-difluoro-5H-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-d]imidazol-6-ylsulfanyl)-furan-2-yl]-8-oxo-4,5,6,7,8,9-hexahydro-2H-pyrrolo[3,4-b]quinoline-3-carboxylic acid ethyl ester. Yield=6%. Analytical LC/MS (method B): m/z=555 (positive ion mode [M+H]+), m/z=553 (negative ion mode [M−H]−).

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 4 h
  3. concentrationThe reaction mixture is then concentrated under reduced pressure
  4. customthe residue is purified on a silica gel column (34 g)
  5. washeluted with a mixture of cyclohexane and ethyl acetate (7/3
  6. additionThe fractions containing the expected product
  7. concentrationare concentrated under reduced pressure
  8. temperatureheated
  9. temperatureat reflux temperature for 30 minutes
  10. filtrationThe insoluble material is collected by filtration
  11. customdried under vacuum

Sources & evidence

ORD record
ord-f1b1508fc65f48149fc876c6c264a094
Source dataset
uspto-grants-2012_04
Patent number
US08163768B2

Reaction notes

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