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

HRID 2416201

Reaktionsgleichung

Reaktionsgleichung von HRID 2416201
C([C:3]1[CH:16]=[CH:15][C:6]([NH:7][C:8]([O:10]C(C)(C)C)=O)=[CH:5][CH:4]=1)#N.S.[C:18]([NH:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=[S:34])[NH2:33])=[CH:28][CH:27]=1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>N1C=CC=CC=1.CO>[C:21]([O:20][C:18](=[O:19])[NH:25][C:26]1[CH:27]=[CH:28][C:29]([C:32]2[S:34][CH:16]=[C:3]([C:4]3[C:8](=[O:10])[NH:7][C:6]4[C:5]([CH:5]=3)=[CH:4][CH:3]=[CH:16][CH:15]=4)[N:33]=2)=[CH:30][CH:31]=1)([CH3:24])([CH3:23])[CH3:22]

Komponenten

6

Edukt 3

HCID 402Hydrogen SulfideHCID 10130644Tert-butyl 4-cyanophenylcarbamateHCID 22638585tert-butyl N-(4-carbamothioylphenyl)carbamate

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of 4-cyano-tert-butyloxycarbonylaniline (2.20 g, 10.0 mmol) in 20 mL of pyridine and 5 mL of TEA was purged with H2S gas for 7.0 h. Solvents were removed under vacuum. The resulting crude 4-Boc-aminobenzene-thiocarboxamide (yellow residue, 70% purity) was used directly in the next step. A solution of 4-Bocamino-benzenethiocarboxamide (205 mg, 70% pure, 0.57 mmol) and 3-(2-bromoacetyl)hydroquinolin-2-one (Example 27b, 78 mg, 0.29 mmol) in 50 mL of MeOH was heated at reflux for 4 h. After cooling to RT, the precipitates were collected by filtration to provide the title compound as an off-white solid. MS m/z: 420.2 (M+1). HRMS m/z: 420.1358 (M+H+, C23H21N3O3S Calc'd 420.1376).

Aufarbeitung

  1. customSolvents were removed under vacuum
  2. temperatureat reflux for 4 h
  3. filtrationthe precipitates were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-a4d0dd2b38ca416c888d782c4b7407e0
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06822097B1

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