Hydrochloric Acid → HCID 58685821, compound

HRID 2249517Notes

Reaction equation

HRID 2249517 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:7]=[C:8]([C:10]([OH:12])=O)[CH:9]=1)=[O:4].C(Cl)(=O)C(Cl)=O.[F:23][C:24]1[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=1[NH2:31].C(N(CC)CC)C.Cl>C(Cl)Cl.CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:7]=[C:8]([C:10](=[O:12])[NH:31][C:25]2[CH:26]=[CH:27][CH:28]=[C:29]([F:30])[C:24]=2[F:23])[CH:9]=1)=[O:4]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 782782,3-DifluoroanilineHCID 586858191-Methanesulfonyl-1H-pyrrole-2,4-dicarboxylic acid 2-methyl ester

Product 1

HCID 58685821HCID 58685821, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-methanesulfonyl-1H-pyrrole-2,4-dicarboxylic acid 2-methyl ester (290 mg, 1.17 mmol) in dry CH2Cl2 (5 mL) and DMF (2 drops) was added oxalyl chloride (220 mg, 1.73 mmol) at room temperature. The mixture was stirred for 1 hour and evaporated. The residue was dried on the vacuum pump for 4 hours and then dissolved in dry CH2Cl2 (5 mL). To this solution was added 2,3-difluoro-phenylamine (300 mg, 2.32 mmol) and triethylamine (240 mg, 2.37 mmol). The reaction mixture was stirred for another 1 hour then poured into 2N HCl solution. The aqueous solution was extracted with EtOAc and the combined organic layers were dried over MgSO4. After removal of solvent by evaporation, the residue was purified by flash column eluting with 20% EtOAc/hexanes to afford the title compound as a yellow solid (410 mg, 98%). MS (ES+): m/e=359.1 (M+H); LC/Method A/3.31 min.

Workup

  1. customevaporated
  2. customThe residue was dried on the vacuum pump for 4 hours
  3. dissolutiondissolved in dry CH2Cl2 (5 mL)
  4. stirringThe reaction mixture was stirred for another 1 hour
  5. extractionThe aqueous solution was extracted with EtOAc
  6. dry with materialthe combined organic layers were dried over MgSO4
  7. customAfter removal of solvent
  8. customby evaporation
  9. customthe residue was purified by flash column
  10. washeluting with 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-de6887101c8b4e6d9b5dcfd7d00d680c
Source dataset
uspto-grants-2008_01
Patent number
US07314885B2

Reaction notes

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