Piperidine → acetic acid 1-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-1-methyl-ethyl ester

HRID 905843

반응식

HRID 905843 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[NH:7][C:6](=[O:12])[CH2:5]2.N1CCCCC1.Cl[C:20]([C:22]([O:25][C:26](=[O:28])[CH3:27])([CH3:24])[CH3:23])=[O:21]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH:11][C:20]([C:22]([O:25][C:26](=[O:28])[CH3:27])([CH3:24])[CH3:23])=[O:21])[NH:7][C:6](=[O:12])[CH2:5]2

참가 물질

5

반응물 3

HCID 8082PiperidineHCID 1234962-Acetoxyisobutyroyl chlorideHCID 101035046-Amino-5-fluoroindolin-2-one

생성물 1

HCID 59250100acetic acid 1-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-1-methyl-ethyl ester수율 99.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-40 °C

실험 절차

A stirred solution of 5-fluoro-6-amino-1,3-dihydro-indol-2-one (410 mg, 2.46 mmol) in 10 ml of tetrahydrofuran was added with piperidine (0.3 ml). The mixture was cooled to −40° C. in an acetone-dry ice bath and added with acetic acid 1-chlorocarbonyl-1-methyl-ethyl ester (405 mg, 2.46 mmol) in 10 ml of tetrahydrofuran dropwise. Upon the completion of the addition, the resulting mixture was stirred at the room temperature overnight until the precipitate was formed. The solid was filtered, washed with water and recrystallized from methanol to give acetic acid 1-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-1-methyl-ethyl ester (720 mg, 99.5%) as a white solid.

후처리

  1. additionUpon the completion of the addition
  2. customwas formed
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customrecrystallized from methanol

출처 및 근거

ORD 기록
ord-032d03c0b0ae423ba66aa3e635e8c7b4
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012966B2

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