Sodium hydride → 4-i-Propyl-phenyl sulfamic acid-[6-[2-(5-trifluoromethyl-pyridin-2-yloxy)ethoxy]-5-(o-methoxy-phenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide

HRID 10253

Reaktionsgleichung

Reaktionsgleichung von HRID 10253
[OH:1][CH2:2][CH2:3][O:4][C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[N:8]=[C:7]([NH:17][S:18](=[O:30])(=[O:29])[NH:19][C:20]2[CH:25]=[CH:24][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=2)[C:6]=1[O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[O:38][CH3:39].[H-].[Na+].[F:42][C:43]([F:52])([F:51])[C:44]1[CH:45]=[CH:46][C:47](Cl)=[N:48][CH:49]=1>C1COCC1>[F:42][C:43]([F:52])([F:51])[C:44]1[CH:45]=[CH:46][C:47]([O:1][CH2:2][CH2:3][O:4][C:5]2[N:10]=[C:9]([C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)[N:8]=[C:7]([NH:17][S:18](=[O:30])(=[O:29])[NH:19][C:20]3[CH:21]=[CH:22][C:23]([CH:26]([CH3:28])[CH3:27])=[CH:24][CH:25]=3)[C:6]=2[O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[O:38][CH3:39])=[N:48][CH:49]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 103028114-i-Propyl-phenyl sulfamic acid-[6-(2-hydroxy-ethoxy)-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide

Produkt 1

HCID 219795814-i-Propyl-phenyl sulfamic acid-[6-[2-(5-trifluoromethyl-pyridin-2-yloxy)ethoxy]-5-(o-methoxy-phenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amideAusbeute 64,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

4-i-Propyl-phenyl sulfamic acid-[6-(2-hydroxy-ethoxy)-5-(o-methoxyphenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide (50 mg, Example 3) was dissolved in THF (8 ml). Sodium hydride (12 mg, 60% dispersion in mineral oil) was added and stirring continued for 10 min. 5-Trifluoromethyl-2-chloro-pyridine (28 mg) was added and the mixture was heated to 60° C. for 180 min. The solvents were evaporated, water (12 ml) and a 10% solution of citric acid was added until the pH was 3. The precipitate was filtered off, washed with water and purified by recrystallization with diethylether to give 4-i-propyl-phenyl sulfamic acid-[6-[2-(5-trifluoromethyl-pyridin-2-yloxy)-ethoxy]-5-(o-methoxy-phenoxy)-2-(4-pyridyl)-pyrimidin-4-yl]-amide (41 mg). tR=5.81 min, (LC); [M+H]+=697.17 (ES+).

Aufarbeitung

  1. customThe solvents were evaporated
  2. additionwater (12 ml) and a 10% solution of citric acid was added until the pH was 3
  3. filtrationThe precipitate was filtered off
  4. washwashed with water
  5. custompurified by recrystallization with diethylether

Quellen und Nachweise

ORD-Eintrag
ord-d0ced6154e874d9fa7cf2d92247c694c
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094781B2

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