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

HRID 2375272노트

반응식

HRID 2375272 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 702Ethanol용매HCID 11723Dimethylethylamine용매HCID 24386Thionyl Chloride용매

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온도
5 °C

실험 절차

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

후처리

  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)

출처 및 근거

ORD 기록
ord-3e69702123f7491984734750e526c53f
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465728B2

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