Diisopropylethylamine → Ethyl 4-[1-[3-[bis(4-isobutylphenyl)methylamino]benzoyl]indolizin-3-yl]butyrate

HRID 1741845Notes

Reaction equation

HRID 1741845 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].C(N(C(C)C)CC)(C)C.[CH2:36]([C:40]1[CH:45]=[CH:44][C:43]([CH:46]([C:48]2[CH:53]=[CH:52][C:51]([CH2:54][CH:55]([CH3:57])[CH3:56])=[CH:50][CH:49]=2)Cl)=[CH:42][CH:41]=1)[CH:37]([CH3:39])[CH3:38]>C(Cl)Cl>[CH2:54]([C:51]1[CH:52]=[CH:53][C:48]([CH:46]([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])[C:43]2[CH:44]=[CH:45][C:40]([CH2:36][CH:37]([CH3:39])[CH3:38])=[CH:41][CH:42]=2)=[CH:49][CH:50]=1)[CH:55]([CH3:57])[CH3:56]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10904244Ethyl 4-[1-(3-aminobenzoyl)indolizin-3-yl]butyrateHCID 19010817Bis(4-isobutylphenyl)chloromethane

Product 1

HCID 11072251Ethyl 4-[1-[3-[bis(4-isobutylphenyl)methylamino]benzoyl]indolizin-3-yl]butyrateYield 48.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of ethyl 4-[1-(3-aminobenzoyl)indolizin-3-yl]butyrate (320 mg) in methylene chloride (10 ml) was added diisopropylethylamine (0.22 ml) and bis(4-isobutylphenyl)chloromethane (340 mg) in methylene chloride (5 ml) at room temperature. After stirring for 18 hours, the reaction mixture was evaporated and extracted with ether. The organic layers were washed with water and brine and dried over sodium sulfate. After evaporation of the solvent, the residue was chromatographed on silica gel (methylene chloride:ethyl acetate=20:1) to give ethyl 4-[1-[3-[bis(4-isobutylphenyl)methylamino]benzoyl]indolizin-3-yl]butyrate (279 mg).

Workup

  1. customthe reaction mixture was evaporated
  2. extractionextracted with ether
  3. washThe organic layers were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was chromatographed on silica gel (methylene chloride:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-bd9d675c0c2540219f7c3fee96c28521
Source dataset
uspto-grants-1994_08
Patent number
US05334716

Reaction notes

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