Trifluoroacetic acid → (R)-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)-N-(pyrrolidin-3-yl)quinolin-8-amine

HRID 1095671노트

반응식

HRID 1095671 반응식
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[C:18]([NH:25][C@H:26]5[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27]5)[CH:19]=[CH:20][CH:21]=4)[N:16]=3)=[CH:13][N:14]=[C:8]2[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][N:9]2[C:12]([C:15]3[CH:24]=[CH:23][C:22]4[C:17](=[C:18]([NH:25][C@@H:26]5[CH2:30][CH2:29][NH:28][CH2:27]5)[CH:19]=[CH:20][CH:21]=4)[N:16]=3)=[CH:13][N:14]=[C:8]2[CH:7]=1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 44185162(S)-tert-butyl 3-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ylamino)pyrrolidine-1-carboxylate

생성물 1

HCID 24996492(R)-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)-N-(pyrrolidin-3-yl)quinolin-8-amine수율 52.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of (S)-tert-butyl 3-(2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinolin-8-ylamino)pyrrolidine-1-carboxylate (0.127 g, 0.252 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (0.389 ml, 5.04 mmol). The resulting mixture was stirred for 2 hours at ambient temperature. The dichloromethane reaction mixture was concentrated under reduced pressure and then diluted with dichloromethane. The resulting solution was washed twice with saturated sodium bicarbonate and twice with a brine solution. The organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification via flash column chromatography (40:1 CH2Cl2/MeOH to 20:1 CH2Cl2/MeOH to 10:1 CH2Cl2/MeOH) produced the title compound (53 mg, 52% Yield). MS APCI (+) m/z 404.3 (M+1) detected.

후처리

  1. concentrationwas concentrated under reduced pressure
  2. additiondiluted with dichloromethane
  3. washThe resulting solution was washed twice with saturated sodium bicarbonate and twice with a brine solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification via flash column chromatography (40:1 CH2Cl2/MeOH to 20:1 CH2Cl2/MeOH to 10:1 CH2Cl2/MeOH)

출처 및 근거

ORD 기록
ord-7b36426d066d4c8a91b9c403fd48573d
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08138181B2

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