Benzoyl chloride → HCID 66973544, 화합물

HRID 1469119노트

반응식

HRID 1469119 반응식
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[C:4](=[O:18])[N:3]=1.CCN(CC)CC.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(Cl)Cl>[C:12]1([S:9]([N:5]2[CH:6]=[C:7]([F:8])[C:2]([NH:1][C:26](=[O:33])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[N:3][C:4]2=[O:18])(=[O:10])=[O:11])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 58138399HCID 58138399, 화합물

생성물 1

HCID 66973544HCID 66973544, 화합물수율 41%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To an 8 mL screw-cap vial was added 4-amino-1-benzenesulfonyl-5-fluoro-1H-pyrimidin-2-one (200 mg, 0.74 mmol), CH2Cl2 (5 mL), Et3N (200 mg, 1.98 mmol), and benzoyl chloride (114 mg, 0.82 mmol). The mixture was shaken at room temperature for 2.5 h, evaporated under a stream of nitrogen, and partitioned between EtOAc and H2O. The organic phase was dried over MgSO4, filtered, and evaporated. The crude material was partially purified by normal phase chromatography (gradient, 10 to 50% EtOAc/petroleum ether), and fractions containing the major product were evaporated and recrystallized from EtOAc and petroleum ether to yield the title product as a white solid (112 mg, 41%): mp 150-151° C.; 1H NMR (300 MHz, CDCl3) δ 8.31-8.25 (m, 2H), 8.24 (d, J=5.8 Hz, 1H), 8.16-8.11 (m, 2H), 7.82-7.75 (m, 1H), 7.68-7.56 (m, 3H), 7.52-7.44 (m, 2H); ESIMS m/z 374 ([M+H]+), 372 ([M−H]−).

후처리

  1. customTo an 8 mL screw-cap vial
  2. customevaporated under a stream of nitrogen
  3. custompartitioned between EtOAc and H2O
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude material was partially purified by normal phase chromatography (gradient, 10 to 50% EtOAc/petroleum ether), and fractions
  8. additioncontaining the major product
  9. customwere evaporated
  10. customrecrystallized from EtOAc and petroleum ether

출처 및 근거

ORD 기록
ord-3072d0a1f4fd4eb49bcbf8958202ac84
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006259B2

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