Methyl(2E)-3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enoate → methyl 3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanoate

HRID 244824노트

반응식

HRID 244824 반응식
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6](/[CH:24]=[CH:25]/[C:26]([O:28][CH3:29])=[O:27])=[CH:5][C:4]=2[N:3]=1>[Pd].CO>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:20][O:21][CH2:22][CH3:23])[N:14]([CH2:15][C:16]([OH:19])([CH3:18])[CH3:17])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:5][C:4]=2[N:3]=1

참가 물질

4

반응물 1

HCID 57657222Methyl(2E)-3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enoate

생성물 1

HCID 57657269methyl 3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanoate

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A glass Parr vessel was charged with 10% palladium on carbon catalyst (0.35 g, 0.1 eq. weight/weight (w/w)), methanol (50 mL) ethanol (50 ml) and Methyl(2E)-3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]prop-2-enoate (3.5 g, 8.8 mmol). The vessel was evacuated and charged with hydrogen gas (45 psi, 3.1×105 Pa). The reaction was shaken at ambient temperature overnight (approximately 18 hours). The reaction mixture was filtered to remove the catalyst and concentrated to dryness. The crude product was purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with 0-30% CMA in chloroform) followed by recrystallization from acetonitrile to provide methyl 3-[4-amino-2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-7-yl]propanoate as a white solid.

후처리

  1. customThe vessel was evacuated
  2. additioncharged with hydrogen gas (45 psi, 3.1×105 Pa)
  3. filtrationThe reaction mixture was filtered
  4. customto remove the catalyst
  5. concentrationconcentrated to dryness
  6. customThe crude product was purified by chromatography
  7. washa HORIZON HPFC system (silica cartridge, eluting with 0-30% CMA in chloroform)
  8. customfollowed by recrystallization from acetonitrile

출처 및 근거

ORD 기록
ord-076cf6e7e686498e9d0484394d908a92
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658666B2

반응 노트

불러오는 중…