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Triethylamine → HCID 71617107, 화합물

HRID 930879
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HRID 930879 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH:20]2[CH2:24][CH2:23][O:22][CH2:21]2)=[C:6]([C:8]2[C:9]3[CH:18]=[CH:17][NH:16][C:10]=3[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)[CH:7]=1.C(N(CC)CC)C.[F:32][CH2:33][CH2:34][S:35](Cl)(=[O:37])=[O:36].[Cl-].[NH4+]>ClCCl>[F:32][CH2:33][CH2:34][S:35]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH:20]2[CH2:24][CH2:23][O:22][CH2:21]2)=[C:6]([C:8]2[C:9]3[CH:18]=[CH:17][NH:16][C:10]=3[C:11](=[O:15])[N:12]([CH3:14])[CH:13]=2)[CH:7]=1)(=[O:37])=[O:36]
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참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 69806Ethanesulfonyl chloride, 2-fluoro-HCID 86721035HCID 86721035, 화합물

생성물 1

HCID 71617107HCID 71617107, 화합물수율 6.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of Example 91b (80.0 mg, 0.246 mmol) and triethylamine (74.6 mg, 0.738 mmol) in dichloromethane (4 mL) was added dropwise 2-fluoroethanesulfonyl chloride (144 mg, 0.984 mmol), and the reaction mixture was stirred at about ambient temperature for about 1 hour. The reaction mixture was neutralized with saturated aqueous ammonium chloride solution (50 mL) and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with saturated aqueous sodium chloride solution, dried (anhydrous magnesium sulfate), filtered, and concentrated. The residue was purified by preparative HPLC (C18, 10-80% acetonitrile in 0.1% TFA/water) to provide the title compound (7.0 mg, 6.5% yield). 1H NMR (300 MHz, CDCl3) ppm 11.54 (bs, 1H), 7.45 (t, J=2.8 Hz, 1H), 7.19 (s, 1H), 6.88 (d, J=8.7 Hz, 1H), 6.73 (d, J=2.7 Hz, 1H) 6.67 (dd, J=3.1, 8.8 Hz, 1H), 6.40 (dd, J=2.0, 2.7 Hz, 1H), 4.76 (m, 1H), 3.82 (s, 3H), 3.85-3.62 (m, 8H), 2.97 (bs, 1H), 2.24-1.85 (m, 2H). MS (ESI+) m/z 436.2 (M+H)+.

후처리

  1. extractionthe mixture was extracted with ethyl acetate (3×50 mL)
  2. washThe combined organic layers were washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by preparative HPLC (C18, 10-80% acetonitrile in 0.1% TFA/water)

출처 및 근거

ORD 기록
ord-cbd6be82466643f796689e208c1bd906
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09296741B2

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