Triethylamine → 4-Amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl methanesulfonate

HRID 336140ノート

反応式

HRID 336140 の反応式
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[NH2:13][C:14]1[C:19]2[C:20]([C:28]3[CH:29]=[N:30][C:31]4[C:36]([CH:37]=3)=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:21]3[N:26]([C:18]=2[N:17]=[CH:16][N:15]=1)[CH2:25][CH:24]([OH:27])[CH2:23][CH2:22]3.C(=O)(O)[O-].[Na+]>C1COCC1>[CH3:8][S:9]([O:27][CH:24]1[CH2:23][CH2:22][C:21]2[N:26]([C:18]3[N:17]=[CH:16][N:15]=[C:14]([NH2:13])[C:19]=3[C:20]=2[C:28]2[CH:29]=[N:30][C:31]3[C:36]([CH:37]=2)=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:25]1)(=[O:11])=[O:10]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 867112804-Amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-ol

生成物 1

HCID 867112814-Amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl methanesulfonate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Triethylamine (0.157 ml) and methanesulfonyl chloride (0.074 ml) were added to a solution of 4-amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-ol (288 mg) obtained in Step 8 in THF (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 ethyl acetate. The organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as a light-brown solid (615 mg).

後処理

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-e0b5e9bdad224a43b4cb5056569659b7
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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