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

HRID 1095671ノート

反応式

HRID 1095671 の反応式
[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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7b36426d066d4c8a91b9c403fd48573d
出典データセット
uspto-grants-2012_03
特許番号
US08138181B2

反応ノート

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