HCID 57826941, compound → HCID 12468202, compound

HRID 422584Notes

Reaction equation

HRID 422584 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1[C:6]2[CH:20]=[C:19]([CH3:21])[S:18][C:7]=2[N:8](C(OC(C)(C)C)=O)[C:9]=1[CH3:10]>C(Cl)Cl>[CH3:21][C:19]1[S:18][C:7]2[NH:8][C:9]([CH3:10])=[C:5]([CH2:4][C:3]([O:2][CH3:1])=[O:22])[C:6]=2[CH:20]=1

Participants

3

Reactant 1

HCID 57826941HCID 57826941, compound

Product 1

HCID 12468202HCID 12468202, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of tert-butyl 4-(2-methoxy-2-oxoethyl)-2,5-dimethyl-6H-thieno[2,3-b]pyrrole-6-carboxylate (0.790 g, 2.443 mmol) in DCM (13.13 mL) was added 13 mL of silica gel. The mixture was concentrated under reduced pressure and the residue was heated to 65° C. under vacuum for 24 h. The reaction mixture was purified by flash chromatography on silica gel (EtOAc/heptane 15/85), to give the title compound (0.35 g, 64%): LC/MS (Table 1, Method a) Rt=2.06 min; MS m/z 222.1 (M−H)−.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customThe reaction mixture was purified by flash chromatography on silica gel (EtOAc/heptane 15/85)

Sources & evidence

ORD record
ord-c5929c22352e4138ab4338d241b2d852
Source dataset
uspto-grants-2012_01
Patent number
US08101645B2

Reaction notes

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