Water → HCID 71666208, 화합물

HRID 929072노트

반응식

HRID 929072 반응식
[CH2:1]([C:4]1([S:7]([NH:10][C:11]2[C:19]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=3[F:28])=[C:18]([F:29])[C:14]3[N:15]=[N:16][S:17][C:13]=3[CH:12]=2)(=[O:9])=[O:8])[CH2:6][CH2:5]1)[CH:2]=[CH2:3].C[N+]1([O-])CC[O:34]CC1.[OH2:38]>C1COCC1.[Os](=O)(=O)(=O)=O>[OH:38][CH:2]([CH2:3][OH:34])[CH2:1][C:4]1([S:7]([NH:10][C:11]2[C:19]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([I:27])=[CH:23][C:22]=3[F:28])=[C:18]([F:29])[C:14]3[N:15]=[N:16][S:17][C:13]=3[CH:12]=2)(=[O:8])=[O:9])[CH2:5][CH2:6]1

참가 물질

6

반응물 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 89705457HCID 89705457, 화합물

생성물 1

HCID 71666208HCID 71666208, 화합물수율 56.5%

시약·촉매·용매 2

HCID 30318Osmium Tetroxide촉매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-allyl-N-(4-fluoro-5-((2-fluoro-4-iodophenyl)amino)benzo[d][1,2,3]thiadiazol-6-yl)cyclopropane-1-sulfonamide (50 mg, 0.09 mmol) in THF (5 mL) was added N-methylmorpholine-N-oxide (12 mg, 0.09 mmol) followed by osmium tetraoxide (5 mg, 0.02 mmol) and water (0.5 mL). The resultant was stirred at room temperature overnight. The mixture was concentrated and then diluted with ethyl acetate. The organic layer was washed with water, saturated NaHCO3 (aq.) and brine sequentially, dried over Na2SO4, filtered and concentrated to give a residue, which was purified by flash chromatography on silica gel to give the product as white solid (30 mg, 56.5% yield). 1H NMR (400 MHz, CDCl3): δ 8.26 (s, 1H), 7.67-7.64 (d, 2H), 7.32 (m, 1H), 7.03 (s, 1H), 6.85 (s, 1H), 4.40-4.26 (m, 2H), 4.20-4.10 (m, 1H), 3.75-3.60 (m, 1H), 3.60-3.50 (m, 1H), 2.62-2.50 (m, 2H), 0.92-0.82 (m, 4H). MS APCI (+) m/z: 583.5, [M+H].

후처리

  1. concentrationThe mixture was concentrated
  2. additiondiluted with ethyl acetate
  3. washThe organic layer was washed with water, saturated NaHCO3 (aq.) and brine sequentially
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a residue, which
  8. customwas purified by flash chromatography on silica gel

출처 및 근거

ORD 기록
ord-c83ac46f6827455b8938401f021d2d85
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290468B2

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