Benzoyl chloride → 1-[6-benzoylamino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 1428874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428874
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:10]([O:12][C:13]([C:15]1[CH:16]=[N:17][N:18]([C:20]2[N:29]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:28](=[O:38])[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([NH2:39])[CH:26]=3)[N:21]=2)[CH:19]=1)=[O:14])[CH3:11]>C(Cl)Cl>[CH2:10]([O:12][C:13]([C:15]1[CH:16]=[N:17][N:18]([C:20]2[N:29]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:28](=[O:38])[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([NH:39][C:1](=[O:8])[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:26]=3)[N:21]=2)[CH:19]=1)=[O:14])[CH3:11]

Komponenten

4

Edukt 2

HCID 7412Benzoyl chlorideHCID 684879131-[6-amino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester

Produkt 1

HCID 684879621-[6-benzoylamino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl esterAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Benzoyl chloride (81.1 μL, 0.698 mmol) was added dropwise to a solution of 1-[6-amino-4-oxo-3-(2-trimethylsilanyl-ethoxymethyl)-3,4-dihydro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid ethyl ester (0.200 g, 0.466 mmol), TEA (0.162 mL, 1.16 mmol), and DCM (2.3 mL). The reaction mixture was stirred at room temperature for 1.5 h and was then diluted with DCM (25 mL) and quenched with water (15 mL). The organic layer was washed with water (20 mL) and brine (20 mL), dried (MgSO4), and concentrated. The residue was purified by FCC (10-70% EtOAc/hexanes) to yield the titled compound (0.240 g, 97% yield). MS (ESI/Cl): mass calcd. for C27H31N5O5Si, 533.2; m/z found, 476.2 [M+H−58]+.

Aufarbeitung

  1. customquenched with water (15 mL)
  2. washThe organic layer was washed with water (20 mL) and brine (20 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by FCC (10-70% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-be7c7556dba14defab04e63697906cf1
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937078B2

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