Dimethylformamide → HCID 9842411, compound

HRID 2084994Notes

Reaction equation

HRID 2084994 reaction equation
FC1C=[C:4]([NH:9][C:10]2[C:11](=[O:23])[NH:12][C:13](=[O:22])[C:14]=2[C:15]2[CH:20]=[CH:19][C:18]([I:21])=[CH:17][CH:16]=2)[CH:5]=CC=1C.CN([CH:27]=[O:28])C>Cl>[CH3:27][O:28][CH2:5][CH2:4][NH:9][C:10]1[C:11](=[O:23])[NH:12][C:13](=[O:22])[C:14]=1[C:15]1[CH:16]=[CH:17][C:18]([I:21])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 22728604HCID 22728604, compound

Product 1

HCID 9842411HCID 9842411, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 3-(3-fluoro-4-methylphenylamino)-4-(4-iodophenyl)-1H-pyrrole-2,5-dione (Example A705, 126 mg, 0.3 mmol) and 2-methoxyethylazine (0.2 mL, 2,3 mmol) in DMF (2 mL) was stirred at room temperature for 113 hours then diluted with hydrochloric acid (0.5M, 50 mL) and extracted with ethyl acetate (50 mL). The ethyl acetate solution was washed with water (2×50 mL) and brine (50 mL), dried over magnesium sulphate and evaporated. The residue was chromatographed on silica gel using dichloromethane-diethyl ether (99:1 v/v) as eluent to afford the title compound, a solid.

Workup

  1. customwas stirred at room temperature for 113 hours
  2. extractionextracted with ethyl acetate (50 mL)
  3. washThe ethyl acetate solution was washed with water (2×50 mL) and brine (50 mL)
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-cd9f7422e706425288f0ccd0c9272482
Source dataset
uspto-grants-2004_04
Patent number
US06719520B2

Reaction notes

Loading…