Trifluoroacetic acid → 7-amino-3-chloro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

HRID 222261노트

반응식

HRID 222261 반응식
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[O:13])[C:11]3[CH:14]=[C:15]([NH:18]CC4C=CC(OC)=CC=4OC)[CH:16]=[CH:17][C:10]=3[CH:9]=[CH:8][C:5]2=[N:6][CH:7]=1.FC(F)(F)C(O)=O>CO.ClCCl>[NH2:18][C:15]1[CH:16]=[CH:17][C:10]2[CH:9]=[CH:8][C:5]3=[N:6][CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]3[C:12](=[O:13])[C:11]=2[CH:14]=1

참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acidHCID 159808203-Chloro-7-[[(2,4-dimethoxyphenyl)methyl]amino]-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

생성물 1

HCID 159808217-amino-3-chloro-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

3-chloro-7-[(2,4-dimethoxybenzyl)amino]-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (1.1 g, 2.7 mmol) was dissolved in 8 mL methanol and 30 mL dichloromethane. Then 10 mL of trifluoroacetic acid was added and the solution was stirred at ambient temperature. After 1 hour, reaction was concentrated, dissolved in 500 mL of ethyl acetate and washed with 200 mL saturated sodium bicarbonate. The organic layer was separated, dried with magnesium sulfate, filtered, and purified by flash column chromatography (0-10% methanol/dichloromethane gradient) and reverse phase HPLC (20-100% acetonitrile/water gradient, 0.1% trifluoroacetic acid modifier) to afford title compound. LRMS (APCI) calculated for C14H10ClN2O [M+H]+, 257.0; found 257.1.

후처리

  1. customreaction
  2. concentrationwas concentrated
  3. dissolutiondissolved in 500 mL of ethyl acetate
  4. washwashed with 200 mL saturated sodium bicarbonate
  5. customThe organic layer was separated
  6. dry with materialdried with magnesium sulfate
  7. filtrationfiltered
  8. custompurified by flash column chromatography (0-10% methanol/dichloromethane gradient)

출처 및 근거

ORD 기록
ord-6cd29ab8117447c4bb9c4271d091a5c4
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207186B2

반응 노트

불러오는 중…