Triethylamine → HCID 66968183, compound

HRID 549334Notes

Reaction equation

HRID 549334 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH2:5][CH:6]1[CH2:11][O:10][CH2:9][CH2:8][NH:7]1)[CH3:2].C(N(CC)CC)C.[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[S:31][C:30]([CH3:32])=[N:29][C:28]=2[C:33](Cl)=[O:34])=[CH:23][CH:22]=1>ClCCl.O>[CH2:1]([O:3][C:4](=[O:12])[CH2:5][CH:6]1[CH2:11][O:10][CH2:9][CH2:8][N:7]1[C:33]([C:28]1[N:29]=[C:30]([CH3:32])[S:31][C:27]=1[C:24]1[CH:25]=[CH:26][C:21]([F:20])=[CH:22][CH:23]=1)=[O:34])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 11789040Ethyl 2-(morpholin-3-yl)acetateHCID 223241192-Methyl-5-(4-fluorophenyl)thiazole-4-carbonyl chloride

Product 1

HCID 66968183HCID 66968183, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Morpholin-3-ylacetic acid ethyl ester Chem Pharm Bull 94, 31(1), 1983 (2.10 g) was dissolved in dichloromethane (50 ml) and treated with triethylamine (1.33 g). The mixture was cooled (ice bath) and 5-(4-fluoro-phenyl)-2-methyl-thiazole-4-carbonyl chloride (1.53 g) in dichloromethane (10 ml) added. The mixture was stirred for 16 h, diluted with water and the organic phase separated. The aqueous phase was extracted with dichloromethane (2×100 ml), the organic phases combined, dried (Na2SO4) and solvent removed at reduced pressure. the residue was column chromatographed (silica gel, 40% ethyl acetate:pentane ˜60% ethyl acetate pentane eluant) to give the title compound (1.46 g).

Workup

  1. additionadded
  2. customthe organic phase separated
  3. extractionThe aqueous phase was extracted with dichloromethane (2×100 ml)
  4. dry with materialdried (Na2SO4) and solvent
  5. customremoved at reduced pressure
  6. customchromatographed (silica gel, 40% ethyl acetate:pentane ˜60% ethyl acetate pentane eluant)

Sources & evidence

ORD record
ord-39468204f0c949e6b1e9896f708fdab9
Source dataset
uspto-grants-2011_05
Patent number
US07943645B2

Reaction notes

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