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Cyclopropanecarbonyl chloride → 3-(1-cyano-1-methylethyl)-N-[3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-d]pyrimidin-5-yl}amino)-4-methylphenyl]benzamide

HRID 1800728
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1800728
[NH2:1][C:2]1[S:3][C:4]2[N:5]=[C:6]([NH:11][C:12]3[CH:13]=[C:14]([NH:19][C:20](=[O:32])[C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])[CH:22]=4)[CH:15]=[CH:16][C:17]=3[CH3:18])[N:7]=[CH:8][C:9]=2[N:10]=1.[CH:33]1([C:36](Cl)=[O:37])[CH2:35][CH2:34]1.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[C:30]([C:27]([C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[C:20]([NH:19][C:14]1[CH:15]=[CH:16][C:17]([CH3:18])=[C:12]([NH:11][C:6]2[N:7]=[CH:8][C:9]3[N:10]=[C:2]([NH:1][C:36]([CH:33]4[CH2:35][CH2:34]4)=[O:37])[S:3][C:4]=3[N:5]=2)[CH:13]=1)=[O:32])([CH3:29])[CH3:28])#[N:31]
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Komponenten

5

Edukt 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 86646090N-{3-[(2-amino[1,3]thiazolo[5,4-d]pyrimidin-5-yl)amino]-4-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide

Produkt 1

HCID 595070373-(1-cyano-1-methylethyl)-N-[3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-d]pyrimidin-5-yl}amino)-4-methylphenyl]benzamideAusbeute 35,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of N-{3-[(2-amino[1,3]thiazolo[5,4-d]pyrimidin-5-yl)amino]-4-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide (137 mg, 309 μmol) in pyridine (3 mL) was added cyclopropanecarbonyl chloride (68 μL, 742 μmol), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution (20 mL), and the mixture was extracted with ethyl acetate/tetrahydrofuran mixture (9:1, 20 mL, 5 mL). The combined organic layer was washed with saturated brine (5 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was recrystallized from methanol and ethyl acetate to give the title compound (56 mg, 35%) as pale-red crystals.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran mixture (9:1, 20 mL, 5 mL)
  2. washThe combined organic layer was washed with saturated brine (5 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was recrystallized from methanol and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-d3b70c9934994ec59175fcbb0b376ebc
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08344135B2

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