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

HRID 219683

반응식

HRID 219683 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 175Acetate용매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b2fbe396834243d48ce1897596814267
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202863B2

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