Hydrochloric Acid → 2-chloro-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno(2,3-b)pyrrole-5-carboxamide

HRID 1178417ノート

反応式

HRID 1178417 の反応式
Cl.CC1(C)[O:7][CH:6]([CH2:8][N:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH:11]([NH:19][C:20]([C:22]3[NH:26][C:25]4[S:27][C:28]([Cl:30])=[CH:29][C:24]=4[CH:23]=3)=[O:21])[C:10]2=[O:31])[CH2:5][O:4]1>C1COCC1>[Cl:30][C:28]1[S:27][C:25]2[NH:26][C:22]([C:20]([NH:19][CH:11]3[CH2:12][C:13]4[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=4)[N:9]([CH2:8][CH:6]([OH:7])[CH2:5][OH:4])[C:10]3=[O:31])=[O:21])=[CH:23][C:24]=2[CH:29]=1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 21906856N-[1-(2,2-Dimethyl-1,3-dioxolan-4-ylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide

生成物 1

HCID 117428502-chloro-N-(1-(2,3-dihydroxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)-6H-thieno(2,3-b)pyrrole-5-carboxamide収率 83%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

6M Aqueous HCl (1.47 mL) was added to N-{1-(2,2-dimethyl-1,3-dioxolan-4-ylmethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide (Method 3; 340 mg, 7.45 mmol) in THF (14 mL) and the reaction was stirred for 4 h. The reaction was quenched by addition of triethylamine (1.5 mL) then diluted with water (30 mL) and EtOAc (40 mL). The organic layer was separated, dried (MgSO4), filtered and evaporated. The residue was triturated with hot Et2O (10 mL) and after cooling was filtered and dried to afford the title compound (260 mg, 83%) as white solid.

後処理

  1. customThe reaction was quenched by addition of triethylamine (1.5 mL)
  2. additionthen diluted with water (30 mL) and EtOAc (40 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was triturated with hot Et2O (10 mL)
  8. temperatureafter cooling
  9. filtrationwas filtered
  10. customdried

出典と根拠

ORDレコード
ord-2c9df474e6ea48ac8afe202108b39e44
出典データセット
uspto-grants-2007_10
特許番号
US07276517B2

反応ノート

読み込み中…