Cornforth reagent → 2-chloro-N-{1-[2-(methylcarbamoyl)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1247518ノート

反応式

HRID 1247518 の反応式
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+:10]1C=CC=C[CH:11]=1.[NH+]1C=CC=CC=1.[Cl:22][C:23]1[S:48][C:26]2[NH:27][C:28]([C:30]([NH:32][CH:33]3[CH2:42][C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[N:35]([CH2:43][CH2:44][CH2:45][OH:46])[C:34]3=[O:47])=[O:31])=[CH:29][C:25]=2[CH:24]=1>CN(C=O)C>[Cl:22][C:23]1[S:48][C:26]2[NH:27][C:28]([C:30]([NH:32][CH:33]3[CH2:42][C:41]4[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=4)[N:35]([CH2:43][CH2:44][C:45]([NH:10][CH3:11])=[O:46])[C:34]3=[O:47])=[O:31])=[CH:29][C:25]=2[CH:24]=1

参加物

4

反応物 2

HCID 2724130Cornforth reagentHCID 10250607HCID 10250607、化合物

生成物 1

HCID 100942462-chloro-N-{1-[2-(methylcarbamoyl)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide収率 61%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Pyridinium dichromate (329 mg, 0.88 mmol) was added to 2-chloro-N-[1-(3-hydroxypropyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-6H-thieno[2,3-b]pyrrole-5-carboxamide (Example 43; 100 mg, 0.248 mmol) in DMF (3 mL) and the reaction was stirred for 24 hours. The reaction was diluted with EtOAC (20 mL) and filtered through celite. The filtrate was washed with 1M HCl (aq.) and the organic layer was dried (MgSO4), filtered and evaporated to afford the crude acid which was used without purification. Standard amide bond formation analogous to Method 3 except using methylamine (2.0 M in THF) as amine gave the title compound (65 mg, 61% over 2 steps) as a white solid.

後処理

  1. additionThe reaction was diluted with EtOAC (20 mL)
  2. filtrationfiltered through celite
  3. washThe filtrate was washed with 1M HCl (aq.)
  4. dry with materialthe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customto afford the crude acid which
  8. customwas used without purification

出典と根拠

ORDレコード
ord-bd02a576caf54d66a9d6c4ffaa508a6a
出典データセット
uspto-grants-2006_10
特許番号
US07129249B2

反応ノート

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