Chlorosulfonic acid → 4-(1,2-Dimethylimidazol-5-yl)-2-{4-[N-(1,3-dimethoxyprop-2-yl)sulphamoyl]anilino}pyrimidine

HRID 2375272ノート

反応式

HRID 2375272 の反応式
Cl[S:2]([OH:5])(=O)=[O:3].[NH:6]([C:13]1[N:18]=[C:17]([C:19]2[N:23]([CH3:24])[C:22]([CH3:25])=[N:21][CH:20]=2)[CH:16]=[CH:15][N:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:26][O:27][CH2:28][CH:29]([NH2:33])[CH2:30][O:31][CH3:32]>S(Cl)(Cl)=O.C(O)C.CN(C)CC>[CH3:24][N:23]1[C:19]([C:17]2[CH:16]=[CH:15][N:14]=[C:13]([NH:6][C:7]3[CH:12]=[CH:11][C:10]([S:2](=[O:5])(=[O:3])[NH:33][CH:29]([CH2:30][O:31][CH3:32])[CH2:28][O:27][CH3:26])=[CH:9][CH:8]=3)[N:18]=2)=[CH:20][N:21]=[C:22]1[CH3:25]

参加物

7

反応物 3

HCID 24638Chlorosulfonic acidHCID 15141601,3-Dimethoxypropan-2-amineHCID 222734802-Anilino-4-(1,2-dimethylimidazol-5-yl)pyrimidine

生成物 1

HCID 693130864-(1,2-Dimethylimidazol-5-yl)-2-{4-[N-(1,3-dimethoxyprop-2-yl)sulphamoyl]anilino}pyrimidine

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 11723Dimethylethylamine溶媒HCID 24386Thionyl Chloride溶媒

反応条件

温度
5 °C

実験手順

Chlorosulphonic acid (230 μl, 3.31 mmol) was added to a solution of the 2-anilino-4-(1,2-dimethylimidazol-5-yl)pyrimidine (Method 34; 300 mg, 1.12 mmol) in thionyl chloride (6 ml) at 5° C. The mixture was stirred at 5° C. for 30 minutes, room temperature for 1 hour and heated at reflux for 1.5 hour. The mixture was allowed to cool to room temperature and a solution of excess 1,3-dimethoxy-2-aminopropane (Method 59) in ethanol (20 ml) and dimethylethylamine (0.5 ml) were added to the residue, and the mixture stirred at room temperature for 18 hours. The volatiles were removed by evaporation. The residue was triturated with water and the solid product collected by filtration and dried under vacuum at 60° C. The residue was purified by flash silica chromatography DCM:MeOH (95:5) to give the title compound. NMR: 2.40 (s, 3H), 3.10 (s, 6H), 3.20(d, 4H), 3.32-3.28 (m, 1H), 3.98 (s, 3H), 7.20 (d, 1H), 7.55 (d, 1H), 7.65 (s, 2H), 7.74 (d, 2H), 7.90 (d, 2H), 8.44 (d, 2H), 9.89 (s, 1H); m/z 447

後処理

  1. temperatureheated
  2. temperatureat reflux for 1.5 hour
  3. temperatureto cool to room temperature
  4. stirringthe mixture stirred at room temperature for 18 hours
  5. customThe volatiles were removed by evaporation
  6. customThe residue was triturated with water
  7. filtrationthe solid product collected by filtration
  8. customdried under vacuum at 60° C
  9. customThe residue was purified by flash silica chromatography DCM:MeOH (95:5)

出典と根拠

ORDレコード
ord-3e69702123f7491984734750e526c53f
出典データセット
uspto-grants-2008_12
特許番号
US07465728B2

反応ノート

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