Triethylamine → HCID 67215335, compound

HRID 2421184Notes

Reaction equation

HRID 2421184 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([C:13]([OH:15])=O)=[C:11]([CH3:16])[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:17][O:18][C:19]1[CH:28]=[C:27]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH:26]=[CH:25][C:20]=1[C:21]([NH:23][NH2:24])=O.[Cl-].ClC1N(C)C=C[N+]=1C.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([C:13]3[O:15][C:21]([C:20]4[CH:25]=[CH:26][C:27]([N:29]5[CH2:34][CH2:33][O:32][CH2:31][CH2:30]5)=[CH:28][C:19]=4[O:18][CH3:17])=[N:23][N:24]=3)=[C:11]([CH3:16])[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 111266512-chloro-1,3-dimethyl-1H-imidazol-3-ium chlorideHCID 242595943-(3-Chlorophenyl)-5-methyl-1,2-oxazole-4-carboxylic acidHCID 67215710HCID 67215710, compound

Product 1

HCID 67215335HCID 67215335, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-(3-chloro-phenyl)-5-methyl-isoxazole-4-carboxylic acid (200 mg, 0.85 mmol) in dichloromethane (4 mL) was added 2-methoxy-4-morpholin-4-yl-benzoic acid hydrazide (266 mg, 0.85 mmol) and 2-chloro-1,3-dimethylimidazolium chloride (313 mg, 1.85 mmol). After the solution was stirred for 15 min at ambient temperature triethylamine (0.59 ml, 4.21 mmol) was added over a period of 2 min and the reaction mixture was stirred for 18 h at this temperature. It was diluted with ethyl acetate (20 mL 1) and washed with aqueous sodium carbonate (half saturated). The aqueous layers were extracted with ethyl acetate. Drying over sodium sulfate and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane=60:20:20 to 0:80:20) afforded the title compound (235 mg, 62%) as a white solid. MS: m/e=453.1 [M+H]+.

Workup

  1. additionwas added over a period of 2 min
  2. washwashed with aqueous sodium carbonate (half saturated)
  3. extractionThe aqueous layers were extracted with ethyl acetate
  4. dry with materialDrying over sodium sulfate and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane=60:20:20 to 0:80:20)

Sources & evidence

ORD record
ord-e9a797ff4f454310adcb7392f18b8504
Source dataset
uspto-grants-2011_06
Patent number
US07956074B2

Reaction notes

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