Ammonium Hydroxide → 2-ethoxymethyl-7-phenyl-1-(piperidin-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine

HRID 9400ノート

反応式

HRID 9400 の反応式
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:29][O:30][CH2:31][CH3:32])[N:14]([CH2:15][CH:16]3[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:5][C:4]=2[N:3]=1.[OH-].[NH4+]>O>[CH2:31]([O:30][CH2:29][C:13]1[N:14]([CH2:15][CH:16]2[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]2)[C:10]2[C:9]3[CH:8]=[CH:7][C:6]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:5][C:4]=3[N:3]=[C:2]([NH2:1])[C:11]=2[N:12]=1)[CH3:32]

参加物

4

反応物 2

HCID 14923Ammonium HydroxideHCID 21984025tert-Butyl 4-[(4-amino-2-ethoxymethyl-7-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate

生成物 1

HCID 100474812-ethoxymethyl-7-phenyl-1-(piperidin-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine収率 54.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

tert-Butyl 4-[(4-amino-2-ethoxymethyl-7-phenyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate (0.64 g) was deprotected according to the method described in Example 177. The crude solid was dissolved in water (10 mL), and ammonium hydroxide was added until the solution was basic. The mixture was then extracted with chloroform (2×10 mL), and the combined extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from acetonitrile and dried for 16 hours in a vacuum oven at 60° C. to provide 0.28 g of 2-ethoxymethyl-7-phenyl-1-(piperidin-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-4-amine as a white, crystalline solid, mp 142–143° C.

後処理

  1. extractionThe mixture was then extracted with chloroform (2×10 mL)
  2. dry with materialthe combined extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from acetonitrile
  6. customdried for 16 hours in a vacuum oven at 60° C.

出典と根拠

ORDレコード
ord-c56825bcfe01483a83fa38235d7cbd81
出典データセット
uspto-grants-2006_08
特許番号
US07091214B2

反応ノート

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