Ethanol → 3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]-N,N-dimethylpropanamide

HRID 244882

반응식

HRID 244882 반응식
C(O)C.[NH2:4][C:5]1[C:14]2[N:15]=[C:16]([CH2:25][CH3:26])[N:17]([CH2:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:13]=2[C:12]2[CH:11]=[CH:10][C:9](/[CH:27]=[CH:28]/[C:29]([N:31]([CH3:33])[CH3:32])=[O:30])=[CH:8][C:7]=2[N:6]=1>[Pd].CO>[NH2:4][C:5]1[C:14]2[N:15]=[C:16]([CH2:25][CH3:26])[N:17]([CH2:18][CH:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)[C:13]=2[C:12]2[CH:11]=[CH:10][C:9]([CH2:27][CH2:28][C:29]([N:31]([CH3:32])[CH3:33])=[O:30])=[CH:8][C:7]=2[N:6]=1

참가 물질

5

반응물 2

HCID 702EthanolHCID 57657266(2E)-3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]-N,N-dimethylprop-2-enamide

생성물 1

HCID 576572373-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]-N,N-dimethylpropanamide수율 68.9%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

A glass Parr bottle was charged with 10% palladium on carbon (0.1 g) wetted with ethanol (10 mL) and a slurry of (2E)-3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]-N,N-dimethylprop-2-enamide (0.32 g, 0.78 mmol) in methanol (200 mL). The vessel was placed on Parr apparatus, evacuated and charged with hydrogen (55 psi). The mixture was shaken at ambient temperature for 48 hours. The reaction mixture was filtered through a 0.2 micron PTFE membrane filter and the filter was rinsed with methanol (100 mL). The filtrate was concentrated to dryness under reduced pressure. The resulting solid was recrystallized from acetonitrile to provide 220 mg of 3-[4-amino-2-ethyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-7-yl]-N,N-dimethylpropanamide as a white crystalline solid, mp 219-220° C.

후처리

  1. customevacuated
  2. additioncharged with hydrogen (55 psi)
  3. filtrationThe reaction mixture was filtered through a 0.2 micron PTFE membrane
  4. filtrationfilter
  5. washthe filter was rinsed with methanol (100 mL)
  6. concentrationThe filtrate was concentrated to dryness under reduced pressure
  7. customThe resulting solid was recrystallized from acetonitrile

출처 및 근거

ORD 기록
ord-874d664fc3bd4326885c37e24acb3d53
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658666B2

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