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m-Chloroperbenzoic acid → N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(phenylsulfonyl)methyl]-1H-1,2,3-triazole-4-carboxamide

HRID 1717360
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HRID 1717360 반응식
[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([NH:29][CH2:30][CH3:31])=[O:28])=[CH:23][CH:22]=3)[C:11]=2[CH2:12][S:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:14])=[O:6])[CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:40])C=1>C1COCC1.C(OCC)(=O)C>[CH:1]1([NH:4][C:5]([C:7]2[N:8]=[N:9][N:10]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([NH:29][CH2:30][CH3:31])=[O:28])=[CH:25][CH:26]=3)[C:11]=2[CH2:12][S:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:40])=[O:14])=[O:6])[CH2:2][CH2:3]1
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5

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 57665018N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(phenylsulfinyl)methyl]-1H-1,2,3-triazole-4-carboxamide

생성물 1

HCID 57665196N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(phenylsulfonyl)methyl]-1H-1,2,3-triazole-4-carboxamide수율 100%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매
HCID 8857
Ethyl Acetate
용매

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온도
0 °C

실험 절차

N-Cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-5-[(phenylsulfinyl)methyl]-1H-1,2,3-triazole-4-carboxamide (107 mg, 0.24 mmol) obtained in Example 313 was dissolved in THF (2.0 ml), m-chloroperbenzoic acid (purity 65%, 64 mg, 0.24 mmol, 1.0 eq.) was added with stirring at 0° C., and the mixture was stirred for 1 hr and at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate (25 ml), washed with 5% aqueous sodium sulfite solution, 2% aqueous sodium carbonate solution and saturated brine, dried over anhydrous sodium sulfate and concentrated. Diethyl ether was added to the residue, and the precipitate was collected by filtration, washed with diethyl ether and dried to give the title compound as a white powder (111 mg, 0.24 mmol, quant.).

후처리

  1. stirringthe mixture was stirred for 1 hr and at room temperature for 2 hr
  2. washwashed with 5% aqueous sodium sulfite solution, 2% aqueous sodium carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. additionDiethyl ether was added to the residue
  6. filtrationthe precipitate was collected by filtration
  7. washwashed with diethyl ether
  8. customdried

출처 및 근거

ORD 기록
ord-4154b80be0b74385b909d824eff18b59
출처 데이터셋
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07803822B2

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