Ethyl Acetate → Ethyl 4-[1-[3-[1-(4-isobutylphenyl)hexylamino]benzoyl]indolizin-3-yl]butyrate

HRID 1741852Notes

Reaction equation

HRID 1741852 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=1)[C:5]([C:7]1[CH:8]=[C:9]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:10]2[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]2)=[O:6].Br[CH:28]([C:34]1[CH:39]=[CH:38][C:37]([CH2:40][CH:41]([CH3:43])[CH3:42])=[CH:36][CH:35]=1)[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].C(N(C(C)C)CC)(C)C.C(OCC)(=O)C>ClCCl.O>[CH2:40]([C:37]1[CH:36]=[CH:35][C:34]([CH:28]([NH:1][C:2]2[CH:3]=[C:4]([CH:24]=[CH:25][CH:26]=2)[C:5]([C:7]2[CH:8]=[C:9]([CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:10]3[C:15]=2[CH:14]=[CH:13][CH:12]=[CH:11]3)=[O:6])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:39][CH:38]=1)[CH:41]([CH3:43])[CH3:42]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 10904244Ethyl 4-[1-(3-aminobenzoyl)indolizin-3-yl]butyrateHCID 109353641-Bromohexyl-4-isobutylbenzene

Product 1

HCID 19010761Ethyl 4-[1-[3-[1-(4-isobutylphenyl)hexylamino]benzoyl]indolizin-3-yl]butyrateYield 60.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 4-[1-(3-aminobenzoyl)indolizin-3-yl]butyrate (175 mg), 1-bromohexyl-4-isobutylbenzene (177 mg) and diisopropylethylamine (194 mg) in dichloromethane (3 ml) was refluxed for 20 hours. The reaction mixture was poured into a mixture of ethyl acetate and water. The organic layer was separated and washed with water and brine, dried over magnesium sulfate and evaporated. The residue was chromatographed on silica gel column eluting with n-hexane and ethyl acetate (3:1) to give ethyl 4-[1-[3-[1-(4-isobutylphenyl)hexylamino]benzoyl]indolizin-3-yl]butyrate (170 mg) as an oil.

Workup

  1. temperaturewas refluxed for 20 hours
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel column
  7. washeluting with n-hexane and ethyl acetate (3:1)

Sources & evidence

ORD record
ord-6b45c29f1be94c968fd559117c73de1b
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

Loading…