Triethylamine → 2-(4-bromo-phenylsulfanyl)-N-[3-(4,5-dihydro-oxazol-2-yl)-1-phenethyl-1H-pyrazol-4-yl]-acetamide

HRID 547514노트

반응식

HRID 547514 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][C:10]([NH:12][C:13]2[C:14]([C:26]([OH:28])=O)=[N:15][N:16]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:17]=2)=[O:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[CH2:33]([N:35](CC)CC)[CH3:34].ClCCN>O1CCCC1.CN(C1C=CC=CN=1)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH2:9][C:10]([NH:12][C:13]2[C:14]([C:26]3[O:28][CH2:34][CH2:33][N:35]=3)=[N:15][N:16]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:17]=2)=[O:11])=[CH:6][CH:7]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 133692-ChloroethylamineHCID 19660Carbonate IonHCID 25009726KR-33494

생성물 1

HCID 250097272-(4-bromo-phenylsulfanyl)-N-[3-(4,5-dihydro-oxazol-2-yl)-1-phenethyl-1H-pyrazol-4-yl]-acetamide수율 99%

시약·촉매·용매 2

HCID 218852-Dimethylaminopyridine촉매HCID 8028Tetrahydrofuran용매

실험 절차

380 mg (0.83 mM) of the compound obtained in Example 23 was dissolved in 1 ml of tetrahydrofuran to which 356 mg (1.65 mM) of di(2-pyridyl (0.1 equivalent)) carbonate and 10 mg (0.08 mM) of dimethylaminopyridine were added dropwise, and the resulting mixture was stirred under a nitrogen atmosphere for 30 minutes. Subsequently, 0.17 ml (1.20 mM) of triethylamine and 144 mg (1.20 mM) of 2-chloroethylamine were added thereto, and the resulting mixture was stirred under a nitrogen atmosphere for 1 hour. The solvent was distilled off under reduced pressure, and the resultant was extracted with ethyl acetate and brine. The organic solvent layer was dried over anhydrous sodium sulfate, filtered, and then distilled under reduced pressure. The resulting impure compound was purified by column chromatography (hexane:ethyl acetate=2:1), to obtain 426 mg (99%) of the title compound.

후처리

  1. additionwere added dropwise
  2. stirringthe resulting mixture was stirred under a nitrogen atmosphere for 1 hour
  3. distillationThe solvent was distilled off under reduced pressure
  4. extractionthe resultant was extracted with ethyl acetate and brine
  5. dry with materialThe organic solvent layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. distillationdistilled under reduced pressure
  8. customThe resulting impure compound was purified by column chromatography (hexane:ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-f8b80ddd4c064fcfb5bd5a6a404d285e
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07939550B2

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