2-Methoxyethylamine → 4-(2-Formyl-1-isopropylimidazol-5-yl)-2-{4-[N-(2-methoxyethyl)sulphamoyl]anilino}pyrimidine

HRID 32348

Reaktionsgleichung

Reaktionsgleichung von HRID 32348
Cl[S:2]([OH:5])(=O)=[O:3].[NH:6]([C:13]1[N:18]=[C:17]([C:19]2[N:23]([CH:24]([CH3:26])[CH3:25])[C:22]([CH:27]=[O:28])=[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.[CH3:29][O:30][CH2:31][CH2:32][NH2:33].C(N(CC)C)C>S(Cl)(Cl)=O.CO>[CH:27]([C:22]1[N:23]([CH:24]([CH3:25])[CH3:26])[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][CH2:32][CH2:31][O:30][CH3:29])=[CH:9][CH:8]=3)[N:18]=2)=[CH:20][N:21]=1)=[O:28]

Komponenten

7

Edukt 4

HCID 80182-MethoxyethylamineHCID 12022DiethylmethylamineHCID 24638Chlorosulfonic acidHCID 116381022-Anilino4-(2-formyl-1-isopropylimidazol-5-yl)pyrimidine

Produkt 1

HCID 866107904-(2-Formyl-1-isopropylimidazol-5-yl)-2-{4-[N-(2-methoxyethyl)sulphamoyl]anilino}pyrimidineAusbeute 24,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 24386Thionyl ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Chlorosulphonic acid (70 μl, 1.0 mmol) was added dropwise to solution of 2-anilino-4-(2-formyl-1-isopropylimidazol-5-yl)pyrimidine (Example 10; 75 mg, 0.24 mmol) in thionyl chloride (2 ml) cooled at 0° C. and the mixture was stirred at 0° C. for 10 minutes then heated at 90° C. for 90 minutes. The volatiles were removed by evaporation and the residue was dried under high vacuum (<2 mmHg) for 1 hour. The resulting solid was placed under nitrogen and a solution of 2-methoxyethylamine (100 μl, 0.5 mmol) and diethylmethylamine (0.5 ml, 7.5 mmol) in MeOH (1.5 ml) added. The mixture was stirred for 30 minutes and the volatiles were evaporated in vacuo. The residue was purified by chromatography eluting with DCM/MeOH (98:2) to give the title compound (26 mg, 24%) as glassy solid. NMR: 1.53 (d, 6H) 2.86 (q, 2H) 3.17 (s, 3H) 3.28 (t, 2H) 5.65 (m, H) 7.3 (t, 1H) 7.50 (t, 1H) 7.71 (d, 2H) 7.83 (s, 1H) 7.89 (d, 2H) 8.68 (d, 1H) 9.81 (s, 1H) 10.11 (s, 1H).

Aufarbeitung

  1. temperaturethen heated at 90° C. for 90 minutes
  2. customThe volatiles were removed by evaporation
  3. customthe residue was dried under high vacuum (<2 mmHg) for 1 hour
  4. stirringThe mixture was stirred for 30 minutes
  5. customthe volatiles were evaporated in vacuo
  6. customThe residue was purified by chromatography
  7. washeluting with DCM/MeOH (98:2)

Quellen und Nachweise

ORD-Eintrag
ord-f37d61d802cf4017b2ed640deadac3b7
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427626B2

Verknüpfte Notizen

Wird geladen…