Trifluoroacetic acid → (2S)-3-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-2-ethylpentan-1-amine

HRID 2035564노트

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HRID 2035564 반응식
[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:20][CH:21]([CH2:34][CH3:35])[C@@H:22]([CH2:32][CH3:33])[CH2:23][NH:24]C(=O)OC(C)(C)C)[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:20][CH:21]([CH2:34][CH3:35])[C@@H:22]([CH2:32][CH3:33])[CH2:23][NH2:24])[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86654357tert-Butyl (2S)-3-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-2-ethylpentylcarbamate

생성물 1

HCID 58303703(2S)-3-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-2-ethylpentan-1-amine수율 29%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

tert-Butyl (2S)-3-(2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-yloxy)-2-ethylpentylcarbamate was dissolved in 5 mL DCM and cooled to 0° C. TFA (5 mL) was added and the mixture was allowed to warm to ambient temperature over 1 hour. The reaction mixture was evaporated to dryness, and the residue was dissolved in 30 mL DCM and washed with 1N NaOH. The combined organic layers were dried over Na2SO4, filtered, and concentrated under vacuum. The residue was purified by silica gel chromatography followed by preparative TLC to give the desired product (42.5 mg, 29%).

후처리

  1. temperatureto warm to ambient temperature over 1 hour
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutionthe residue was dissolved in 30 mL DCM
  4. washwashed with 1N NaOH
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-8f3960dd163f4dc6b4cb7f407eface45
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575145B2

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