Acryloyl chloride → N-(4-amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl)acrylamide

HRID 336143ノート

反応式

HRID 336143 の反応式
C(N(CC)C(C)C)(C)C.[C:10](Cl)(=[O:13])[CH:11]=[CH2:12].[N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[C:17]([C:25]2[C:26]3[C:38]([NH2:39])=[N:37][CH:36]=[N:35][C:27]=3[N:28]3[C:33]=2[CH2:32][CH2:31][CH:30]([NH2:34])[CH2:29]3)[CH:16]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[NH2:39][C:38]1[C:26]2[C:25]([C:17]3[CH:16]=[N:15][C:24]4[C:19]([CH:18]=3)=[CH:20][CH:21]=[CH:22][CH:23]=4)=[C:33]3[N:28]([C:27]=2[N:35]=[CH:36][N:37]=1)[CH2:29][CH:30]([NH:34][C:10](=[O:13])[CH:11]=[CH2:12])[CH2:31][CH2:32]3

参加物

6

反応物 4

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 867112835-(Quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizine-4,8-diamine

生成物 1

HCID 78149057N-(4-amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl)acrylamide

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

N,N-diisopropylethylamine (0.033 ml) and acryloyl chloride (0.0154 ml) were added to a solution of 5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizine-4,8-diamine (68 mg) obtained in Step 11 in chloroform (2.5 ml) under ice-cooling. After stirring at the same temperature for 15 minutes, the mixture was poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: chloroform/methanol) to obtain the title compound as a yellow solid (35.4 mg).

後処理

  1. temperaturecooling
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was then distilled off under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (developing solvent: chloroform/methanol)

出典と根拠

ORDレコード
ord-3b2a9dba8a9b44aeb267ed5b1867da5e
出典データセット
uspto-grants-2014_11
特許番号
US08889666B2

反応ノート

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