(4-[4-(2-Oxo-1,2-dihydro-quinolin-3-yl)-thiazol-2-yl]-phenyl)-carbamic acid tert-butyl ester → 3-[2-(4-Amino-phenyl)-thiazol-4-yl]-1H-quinolin-2-one

HRID 2416202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2416202
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][CH:16]=[C:17]([C:19]3[C:20](=[O:29])[NH:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:18]=2)=[CH:10][CH:9]=1)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:15][CH:16]=[C:17]([C:19]3[C:20](=[O:29])[NH:21][C:22]4[C:27]([CH:28]=3)=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:18]=2)=[CH:10][CH:9]=1

Komponenten

4

Edukt 1

HCID 58810140(4-[4-(2-Oxo-1,2-dihydro-quinolin-3-yl)-thiazol-2-yl]-phenyl)-carbamic acid tert-butyl ester

Produkt 1

HCID 101497433-[2-(4-Amino-phenyl)-thiazol-4-yl]-1H-quinolin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of {4-[4-(2-oxo-1,2-dihydro-quinolin-3-yl)-thiazol-2-yl]-phenyl}-carbamic acid tert-butyl ester (Example 97, 70 mg, 0.17 mmol) in 0.8 mL of CH2Cl2 and 0.8 mL of TFA was stirred at RT for 1 h. Solvents were removed under vacuum and the residue was azeotroped twice with toluene. To the flask, 4.0 mL of aqueous HCl (1 M) was added and solids formed. The solvent was removed again and the solid was azeotroped with toluene twice. The solid was dried under vacuum overnight to afford the title compound as a light yellow solid. MS m/z: 320.2 (M+1). Anal. Calc'd for C18H13N3OS.0.8H2O.1.6HBr: C, 55.13; H, 4.16; N, 10.72; O, 7.34; S, 8.18. Found: C, 55.24; H, 4.15; N, 10.66; O, 7.45; S, 8.21.

Aufarbeitung

  1. customSolvents were removed under vacuum
  2. customthe residue was azeotroped twice with toluene
  3. additionTo the flask, 4.0 mL of aqueous HCl (1 M) was added
  4. customsolids formed
  5. customThe solvent was removed again
  6. customthe solid was azeotroped with toluene twice
  7. customThe solid was dried under vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-dbd737f8962f4d6baa76ba3ef44e7b8b
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06822097B1

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