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

HRID 219683

反応式

HRID 219683 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 175Acetate溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b2fbe396834243d48ce1897596814267
出典データセット
uspto-grants-2012_06
特許番号
US08202863B2

関連ノート

読み込み中…