Methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate → HCID 68766620, compound

HRID 2391727Notes

Reaction equation

HRID 2391727 reaction equation
[N:1]1([CH2:7][CH2:8][NH:9][C:10]([C:12]2[N:17]=[CH:16][C:15]3[N:18]=[CH:19][NH:20][C:14]=3[CH:13]=2)=[O:11])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:22]1([C:28]([O:30][CH3:31])=[O:29])[C:26](=[O:27])[CH:25]=[CH:24][S:23]1>C(Cl)(Cl)Cl>[OH:27][C:26]1[CH:25]=[C:24]([N:20]2[C:14]3[CH:13]=[C:12]([C:10](=[O:11])[NH:9][CH2:8][CH2:7][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)[N:17]=[CH:16][C:15]=3[N:18]=[CH:19]2)[S:23][C:22]=1[C:28]([O:30][CH3:31])=[O:29]

Participants

4

Reactant 2

HCID 15588102Methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylateHCID 178523408HCID 178523408, compound

Product 1

HCID 68766620HCID 68766620, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 2.27 g of 1H-imidazo[4,5-c]pyridine-6-carboxylic acid (2-morpholin-4-yl-ethyl)-amide in 150 ml chloroform was slowly added a solution of 1.27 g of methyl 2-chloro-3-oxo-2,3-dihydrothiophene-2-carboxylate in 100 ml chloroform and the reaction mixture was stirred for 12 h at room temperature. The reaction mixture was washed with water (3×50 ml) and the organic layer was dried with MgSO4 and concentrated under vacuum. The residue was dissolved in dichloromethane and purified by flash chromatography (dichloromethane/methanol, elution gradient 10/0 to 9/1 (v/v))) to give the title compound.

Workup

  1. washThe reaction mixture was washed with water (3×50 ml)
  2. dry with materialthe organic layer was dried with MgSO4
  3. concentrationconcentrated under vacuum
  4. dissolutionThe residue was dissolved in dichloromethane
  5. custompurified by flash chromatography (dichloromethane/methanol, elution gradient 10/0 to 9/1 (v/v)))

Sources & evidence

ORD record
ord-55296e476c124732a1e2e11f0c462525
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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