Triethylamine → 4(5-Phenylmethylthio-7-chloro-thiazolo[4,5-d]pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1831464

Reaktionsgleichung

Reaktionsgleichung von HRID 1831464
[C:1]1([CH2:7][S:8][C:9]2[N:10]=[C:11]([Cl:19])[C:12]3[S:17][C:16](Br)=[N:15][C:13]=3[N:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:20][CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1.C(N(CC)CC)C>C(#N)C>[C:30]([O:29][C:27]([N:24]1[CH2:25][CH2:26][CH:21]([NH:20][C:16]2[S:17][C:12]3[C:11]([Cl:19])=[N:10][C:9]([S:8][CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[N:14][C:13]=3[N:15]=2)[CH2:22][CH2:23]1)=[O:28])([CH3:33])([CH3:31])[CH3:32]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 220520385-(Benzylthio)-2-bromo-7-chlorothiazolo[4,5-d]pyrimidine

Produkt 1

HCID 867601104(5-Phenylmethylthio-7-chloro-thiazolo[4,5-d]pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl esterAusbeute 57,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

5-Phenylmethylthio-2-bromo-7-chloro-thiazolo[4,5-d]pyrimidine (WO 00/09511) (525 mg, 1.4 mmol), 4-amino-1-N-Boc-piperidine (339 mg, 1.7 mmol) and triethylamine (196 μL, 1.4 mmol) were dissolved in anhydrous acetonitrile (15 mL) and the mixture was stirred under a nitrogen atmosphere at 35° C. for 24 hours. The mixture was filtered and the remaining solid was washed with acetonitrile. After drying in air for 48 hours, 396 mg (57% yield) of the title compound was obtained as a white solid.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. washthe remaining solid was washed with acetonitrile
  3. customAfter drying in air for 48 hours

Quellen und Nachweise

ORD-Eintrag
ord-9eec80bca90e411aae41bd6949dce338
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07067657B2

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