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Sodium Carbonate → Butyl [3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methylphenyl]carbamate

HRID 1800504
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1800504
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([O:11][C:12]1[CH:13]=[C:14]([NH:19][C:20](=[O:26])[O:21]C(C)(C)C)[CH:15]=[CH:16][C:17]=1[CH3:18])[N:5]=2.[CH:27]1([C:30](Cl)=[O:31])[CH2:29][CH2:28]1.C(=O)([O-])[O-].[Na+].[Na+]>N1C=CC=CC=1.CO>[CH:27]1([C:30]([NH:1][C:2]2[S:3][C:4]3[C:9]([N:10]=2)=[CH:8][CH:7]=[C:6]([O:11][C:12]2[CH:13]=[C:14]([NH:19][C:20](=[O:26])[O:21][CH2:6][CH2:7][CH2:8][CH3:9])[CH:15]=[CH:16][C:17]=2[CH3:18])[N:5]=3)=[O:31])[CH2:29][CH2:28]1
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Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 77637Cyclopropanecarbonyl chlorideHCID 86646011Tert-butyl {3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-methylphenyl}carbamate

Produkt 1

HCID 86646012Butyl [3-({2-[(cyclopropylcarbonyl)amino][1,3]thiazolo[5,4-b]pyridin-5-yl}oxy)-4-methylphenyl]carbamateAusbeute 186,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887
Methanol
Lösungsmittel
HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl {3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-methylphenyl}carbamate (800 mg, 2.14 mmol) in pyridine (10 mL) was added cyclopropanecarbonyl chloride (390 μL, 4.29 mmol), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was diluted with methanol (20 mL), anhydrous sodium carbonate (1.0 g, 9.43 mmol) was added, and the mixture was stirred at room temperature for 6 hr. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was diluted with ethyl acetate (100 mL)/tetrahydrofuran (10 mL), washed with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 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 triturated with ethyl acetate and diisopropyl ether to give the title compound (880 mg, 93%) as a pale-yellow powder.

Aufarbeitung

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for 6 hr
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionThe obtained residue was diluted with ethyl acetate (100 mL)/tetrahydrofuran (10 mL)
  6. washwashed with 5% aqueous sodium hydrogen carbonate solution (100 mL) and saturated brine (100 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe insoluble material was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure
  10. customThe obtained residue was triturated with ethyl acetate and diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-c797a762040845b0b1466e35a02e789a
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08344135B2

Notizen zur Reaktion

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