Diisopropylethylamine → 4-methyl-6-{6-[4-(5-oxo-3-phenyl-4,5-dihydro-1,2,4-triazol-1-yl)-piperidin-1-yl]-pyrimidine-4-carbonyl}-3H-benzoxazol-2-one

HRID 469374

Reaktionsgleichung

Reaktionsgleichung von HRID 469374
[C:1]1([C:7]2[NH:8][C:9](=[O:18])[N:10]([CH:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:20]1[N:25]=[CH:24][N:23]=[C:22]([C:26]([C:28]2[CH:37]=[C:36]([CH3:38])[C:31]3[NH:32][C:33](=[O:35])[O:34][C:30]=3[CH:29]=2)=[O:27])[CH:21]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:38][C:36]1[C:31]2[NH:32][C:33](=[O:35])[O:34][C:30]=2[CH:29]=[C:28]([C:26]([C:22]2[CH:21]=[C:20]([N:15]3[CH2:14][CH2:13][CH:12]([N:10]4[C:9](=[O:18])[NH:8][C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)=[N:11]4)[CH2:17][CH2:16]3)[N:25]=[CH:24][N:23]=2)=[O:27])[CH:37]=1

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 581812066-(6-chloropyrimidine-4-carbonyl)-4-methyl-3H-benzoxazol-2-oneHCID 135627598HCID 135627598, Verbindung

Produkt 1

HCID 1359214094-methyl-6-{6-[4-(5-oxo-3-phenyl-4,5-dihydro-1,2,4-triazol-1-yl)-piperidin-1-yl]-pyrimidine-4-carbonyl}-3H-benzoxazol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

378 mg (1.00 mmol) 5-phenyl-2-piperidin-4-yl-2,4-dihydro-1,2,4-triazol-3-one, 289 mg (1.00 mmol) 6-(6-chloropyrimidine-4-carbonyl)-4-methyl-3H-benzoxazol-2-one and 0.348 mL (2.0 mmol) DIPEA were stirred overnight in 10 mL DMF at RT. The mixture was purified by preparative HPLC-MS. The fractions containing the product were combined, the organic solvent was eliminated i. vac. and the aqueous phase remaining was neutralised with a 4N aqueous NaOH solution. The precipitate was suction filtered, washed with water and dried in the CAD.

Aufarbeitung

  1. customThe mixture was purified by preparative HPLC-MS
  2. additionThe fractions containing the product
  3. filtrationfiltered
  4. washwashed with water
  5. customdried in the CAD

Quellen und Nachweise

ORD-Eintrag
ord-b2ed7abcd8b94958944d7d065c7cc43e
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629137B2

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