3-(1,3,2-Dioxaborinan-2-yl)pyridine → tert-butyl 4-{[4-amino-2-ethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}piperidine-1-carboxylate

HRID 9442

反応式

HRID 9442 の反応式
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:29][CH3:30])[N:14]([CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[C:10]=2[C:9]2[CH:8]=[CH:7][C:6](Br)=[CH:5][C:4]=2[N:3]=1.B1([C:38]2[CH:43]=[CH:42][CH:41]=[N:40][CH:39]=2)OCCCO1>O>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:29][CH3:30])[N:14]([CH2:15][CH:16]3[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:38]3[CH:39]=[N:40][CH:41]=[CH:42][CH:43]=3)=[CH:5][C:4]=2[N:3]=1

参加物

4

反応物 2

HCID 41980053-(1,3,2-Dioxaborinan-2-yl)pyridineHCID 21984269tert-Butyl 4-[(4-amino-7-bromo-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate

生成物 1

HCID 21984221tert-butyl 4-{[4-amino-2-ethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}piperidine-1-carboxylate収率 59.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

tert-Butyl 4-[(4-amino-7-bromo-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)methyl]piperidine-1-carboxylate (9.24 g, 18.9 mmol) and pyridine-3-boronic acid 1,3-propanediol cyclic ester (3.39 g, 20.8 mmol) were coupled according to the method described in Examples 118–121. Additional reagents were added after the reaction was heated for 16 hours, and the reaction was continued for 16 hours. Water (20 mL) was added, and the n-propanol was removed under reduced pressure. The remaining mixture was extracted with chloroform (2×200 mL), and the combined organic fractions were purified by column chromatography on silica gel (eluting with chloroform and chloroform:CMA). The resulting solid was recrystallized from acetonitrile to provide 5.44 g of tert-butyl 4-{[4-amino-2-ethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]methyl}piperidine-1-carboxylate as a white, fluffy solid, mp 229–231° C.

後処理

  1. additionAdditional reagents were added after the reaction
  2. temperaturewas heated for 16 hours
  3. customthe n-propanol was removed under reduced pressure
  4. extractionThe remaining mixture was extracted with chloroform (2×200 mL)
  5. customthe combined organic fractions were purified by column chromatography on silica gel (eluting with chloroform and chloroform:CMA)
  6. customThe resulting solid was recrystallized from acetonitrile

出典と根拠

ORDレコード
ord-6ab58770b4c24ae7b57719be753f7eac
出典データセット
uspto-grants-2006_08
特許番号
US07091214B2

関連ノート

読み込み中…