Trifluoroacetic acid → 1-isopropyl-1H-imidazo[4,5-c]pyridin-6-amine

HRID 1778021노트

반응식

HRID 1778021 반응식
FC(F)(F)C(O)=O.[CH:8]([N:11]1[C:19]2[CH:18]=[C:17]([NH:20]CC3C=CC(OC)=CC=3)[N:16]=[CH:15][C:14]=2[N:13]=[CH:12]1)([CH3:10])[CH3:9]>C(Cl)Cl>[CH:8]([N:11]1[C:19]2[CH:18]=[C:17]([NH2:20])[N:16]=[CH:15][C:14]=2[N:13]=[CH:12]1)([CH3:10])[CH3:9]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 1180368001-isopropyl-N-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridin-6-amine2회

생성물 1

HCID 840632621-isopropyl-1H-imidazo[4,5-c]pyridin-6-amine

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
40 °C

실험 절차

Trifluoroacetic acid (2.42 ml, 31.4 mmol) was added to a solution of 1-isopropyl-N-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridin-6-amine (intermediate 25, 596 mg, 2.01 mmol) in DCM (12 ml) and then the mixture was stirred at 40° C. for 24 h. The reaction mixture was diluted with DCM and washed with sat. aq. NaHCO3 (strong gas evolution) and H2O. The aqueous phase was extracted with DCM (2×). The combined organic layers were dried over Na2SO4 and evaporated. The crude material was applied to a 24 g RediSep® silica column and purified by normal phase chromatography, eluting with 9:1 CH2Cl2/MeOH. Product-containing fractions were combined and evaporated to give the title compound as a beige solid. (UPLC-MS 6) tR 0.33; ESI-MS 177.1 [M+H]+.

후처리

  1. washwashed with sat. aq. NaHCO3 (strong gas evolution) and H2O
  2. extractionThe aqueous phase was extracted with DCM (2×)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customevaporated
  5. custompurified by normal phase chromatography
  6. washeluting with 9:1 CH2Cl2/MeOH
  7. customevaporated

출처 및 근거

ORD 기록
ord-3665b3dd60ef4c95a35e214625261c39
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266883B2

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