Hydrochloric Acid → 2-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid 3-acetylsulfamoyl-benzylamide

HRID 219683Notes

Reaction equation

HRID 219683 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([NH:10][S:11]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH2:21])[CH:15]=1)(=[O:13])=[O:12])(=[O:9])[CH3:8].[F:22][C:23]1[CH:24]=[C:25]([C:29]2[N:34]=[CH:33][C:32]([C:35](Cl)=[O:36])=[CH:31][N:30]=2)[CH:26]=[CH:27][CH:28]=1.Cl>CCOC(C)=O.O.C([O-])(=O)C>[C:7]([NH:10][S:11]([C:14]1[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=1)[CH2:20][NH:21][C:35]([C:32]1[CH:33]=[N:34][C:29]([C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([F:22])[CH:24]=2)=[N:30][CH:31]=1)=[O:36])(=[O:12])=[O:13])(=[O:9])[CH3:8]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 69122572N-acetyl-3-aminomethyl-benzenesulfonamideHCID 874965532-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid chloride

Product 1

HCID 166661002-(3-Fluoro-phenyl)-pyrimidine-5-carboxylic acid 3-acetylsulfamoyl-benzylamide

Reagents, catalysts & solvents 3

HCID 175AcetateSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of potassium carbonate (1.22 mmol) and N-acetyl-3-aminomethyl-benzenesulfonamide (1.22 mmol) in EtOAc (10 mL) and water (10 mL) is added a solution of 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid chloride (1.22 mmol) in acetate (10 mL) at 0° C., and the mixture is stirred at room temperature overnight. The mixture is acidified with 5% HCl to pH ˜2-3 and extracted with EtOAc. The organic layer is separated, washed with water and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue is purified by silica gel column chromatography eluting with EtOAc to afford 2-(3-fluoro-phenyl)-pyrimidine-5-carboxylic acid 3-acetylsulfamoyl-benzylamide as a solid. MS: 429 (M+H); 1H NMR (300 MHz, CD3OD): δ 3.95-4.00 (d, 3H), 4.85 (s, 3H), 7.22-7.34 (m, H), 7.41-7.62 (m, H), 7.66-7.83 (d, 2H), 7.88-7.95 (d, H), 8.04 (s, H), 8.12-8.23 (m, H), 8.26-8.37 (d, H), 9.26-9.34 (m, 2H).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer is separated
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by silica gel column chromatography
  8. washeluting with EtOAc

Sources & evidence

ORD record
ord-b2fbe396834243d48ce1897596814267
Source dataset
uspto-grants-2012_06
Patent number
US08202863B2

Reaction notes

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