Acetyl chloride → {1-[4-(2-Acetylamino-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl Ester

HRID 2362174Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2362174
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:22][N:21]4[N:30]=[C:31]([NH2:33])[N:32]=[C:20]4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[C:35](Cl)(=[O:37])[CH3:36]>CN(C1C=CN=CC=1)C.O1CCOCC1.C(Cl)Cl>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:23]([C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:22][N:21]4[N:30]=[C:31]([NH:33][C:35](=[O:37])[CH3:36])[N:32]=[C:20]4[N:19]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

6

Edukt 2

HCID 6367Acetyl chlorideHCID 66823557HCID 66823557, Verbindung

Produkt 1

HCID 66823339{1-[4-(2-Acetylamino-6-phenyl-[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)-phenyl]-cyclobutyl}-carbamic Acid Tert-butyl EsterAusbeute 58,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To the solution of 6-1 (100 mg, 0.22 mmol) and Et3 N (0.2 mL) DMAP (2 mg) in dioxane (2 mL) was added acetyl chloride (21 mg, 0.25 mmol) and the mixture was heated at 100° C. for 10 h. The mixture was diluted with 20 mL of DCM, the combined organic phase was washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep.TLC to give 64 mg of 6-3.

Aufarbeitung

  1. washthe combined organic phase was washed with brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by prep.TLC

Quellen und Nachweise

ORD-Eintrag
ord-528453549bd54509bb67ee7f1a23d294
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08691825B2

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