Potassium Carbonate → HCID 25181715, compound

HRID 1697067Notes

Reaction equation

HRID 1697067 reaction equation
C([O-])([O-])=O.[K+].[K+].[CH3:7][O:8][C:9](=[O:45])[C:10]([N:12]([C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[C:26](=[O:44])[CH2:27][CH2:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](=[O:43])(=[O:42])[NH:36][CH2:37][CH:38]([OH:41])[CH2:39][OH:40])=[CH:31][CH:30]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.COC(=O)C(N(C1C=C(Cl)C=CC=1C(=O)CCC1C=CC(S(=O)(=O)NCC2COC(C)(C)O2)=CC=1)C1C=CC=CC=1)=O>CO>[CH3:7][O:8][C:9]([C:10]1[N:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19]2[C:20]([C:26](=[O:44])[C:27]=1[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](=[O:43])(=[O:42])[NH:36][CH2:37][CH:38]([OH:41])[CH2:39][OH:40])=[CH:31][CH:30]=1)=[CH:21][CH:22]=[C:23]([Cl:25])[CH:24]=2)=[O:45]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 59846279HCID 59846279, compoundHCID 66815803HCID 66815803, compound

Product 1

HCID 25181715HCID 25181715, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

K2CO3 (12 mg) was added the mixture of N-(5-chloro-2-{3-[4-(2,3-dihydroxy-propylsulfamoyl)-phenyl]-propionyl}-phenyl)-N-phenyl-oxalamic acid methyl ester and N-(5-chloro-2-{3-[4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethylsulfamoyl)-phenyl]-propionyl}-phenyl)-N-phenyl-oxalamic acid methyl ester (0.05 mmol) in MeOH (5 mL), and the resulting mixture stirred at 80° C. for 1.5 h. The reaction mixture was then cooled and evaporated under reduced pressure. The residue was partitioned between water and EtOAc, the organic layer separated, and the aqueous layer extracted with EtOAc (2×25 mL). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified twice by preparative TLC (DCM/MeOH, 9:1) and then (DCM/MeOH, 95:5) to provide 7-chloro-3-[4-(2,3-dihydroxy-propylsulfamoyl)-benzyl]-4-oxo-1-phenyl-1,4-di-hydroquinoline-2-carboxylic acid methyl ester as light brown powder. MS=556.8 [M+H]+ and 554.9 [M−H]−.

Workup

  1. temperatureThe reaction mixture was then cooled
  2. customevaporated under reduced pressure
  3. customThe residue was partitioned between water and EtOAc
  4. customthe organic layer separated
  5. extractionthe aqueous layer extracted with EtOAc (2×25 mL)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customThe crude residue was purified twice by preparative TLC (DCM/MeOH, 9:1)

Sources & evidence

ORD record
ord-93c84d467be849a1876e9c3503d1dd62
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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