Morpholine → HCID 67756016, compound

HRID 2372386Notes

Reaction equation

HRID 2372386 reaction equation
[CH:1]([O:4][C:5]([C:7]1[C:8]([CH3:19])=[CH:9][N:10]2[CH:14]([CH2:15][C:16]([OH:18])=O)[CH2:13][S:12][C:11]=12)=[O:6])([CH3:3])[CH3:2].[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH:1]([O:4][C:5]([C:7]1[C:8]([CH3:19])=[CH:9][N:10]2[CH:14]([CH2:15][C:16]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:18])[CH2:13][S:12][C:11]=12)=[O:6])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 10868DicyclohexylcarbodiimideHCID 19903387HCID 19903387, compound

Product 1

HCID 67756016HCID 67756016, compoundYield 54.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.54 g of (7-isopropoxycarbonyl-6-methyl-2,3-dihydropyrrolo[2,1-b]thiazol-3-yl)acetic acid, 0.70 g of morpholine and 0.12 g of 4-N,N-dimethylaminopyridine were dissolved in 50 ml of dichloromethane. 1.44 g of N,N'-dicyclohexylcarbodiimide was added thereto under ice-cooling and stirring. Then the mixture was stirred at room temperature for 9 days. After filtering off the insoluble matters, the solvent was distilled off. The oily residue thus obtained was purified by silica gel column chromatography. After crystallizing from ether/n-hexane, 1.05 g of the title compound was obtained.

Workup

  1. temperatureunder ice-cooling
  2. stirringThen the mixture was stirred at room temperature for 9 days
  3. filtrationAfter filtering off the insoluble matters
  4. distillationthe solvent was distilled off
  5. customThe oily residue thus obtained
  6. customwas purified by silica gel column chromatography
  7. customAfter crystallizing from ether/n-hexane

Sources & evidence

ORD record
ord-7d04c969db48418d81b8d8d3fc24d692
Source dataset
uspto-grants-1992_03
Patent number
US05098919

Reaction notes

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