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 1178435Notes

Reaction equation

HRID 1178435 reaction equation
[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

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 10250607HCID 10250607, compound

Product 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-carboxamideYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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 THE) as amine gave the title compound (65 mg, 61% over 2 steps) as a white solid.

Workup

  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

Sources & evidence

ORD record
ord-253b26dcf8004ebaa78a725c9aacfdfc
Source dataset
uspto-grants-2007_10
Patent number
US07276517B2

Reaction notes

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