Pyridine → 4-(2-Fluoro-4-benzyloxycarbonylaminophenyl)-3,6-dihydro-2H-thiopyran

HRID 723810노트

반응식

HRID 723810 반응식
[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH2:10][CH2:11][S:12][CH2:13][CH:14]=1.N1C=CC=CC=1.Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH:5]=[CH:4][C:3]=1[C:9]1[CH2:14][CH2:13][S:12][CH2:11][CH:10]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 112295653-Fluoro-4-(3,6-dihydro-2h-thiopyran-4-yl)benzenamine

생성물 1

HCID 112564024-(2-Fluoro-4-benzyloxycarbonylaminophenyl)-3,6-dihydro-2H-thiopyran

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

4-(2-Fluoro-4-aminophenyl)-3,6-dihydro-2H-thiopyran (9.8 g, 46.8 mM) was dissolved in dry dichloromethane (196 ml), pyridine (6.23 g, 79.1 mM) added, and the mixture stirred under nitrogen at −20°. A solution of benzyl chloroformate (9.54 g, 53.9 mM) dissolved in dry dichloromethane (25 ml) was added dropwise, and the mixture left to warm to ambient temperature over 18 hours. The mixture was washed with 1M hydrochloric acid (200 ml), then brine (100 ml), dried (magnesium sulfate), filtered and evaporated to a small volume. The addition of isohexane (300 ml) precipitated the desired product (15.5 g).

후처리

  1. additionwas added dropwise
  2. waitthe mixture left
  3. washThe mixture was washed with 1M hydrochloric acid (200 ml)
  4. dry with materialbrine (100 ml), dried (magnesium sulfate)
  5. filtrationfiltered
  6. customevaporated to a small volume
  7. additionThe addition of isohexane (300 ml)
  8. customprecipitated the desired product (15.5 g)

출처 및 근거

ORD 기록
ord-44fd2d03c1be4fb1b17bd286c6d4f1ce
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141583B2

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