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

反応式

HRID 244882 の反応式
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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-874d664fc3bd4326885c37e24acb3d53
出典データセット
uspto-grants-2014_02
特許番号
US08658666B2

関連ノート

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