Dimethylformamide → [4-(Benzyloxy)-5-methoxy-2-nitrophenyl][4-(4-quinazolinyl)piperazino]methanone

HRID 1876823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1876823
CN(C=O)C.[C:6]([O:14][C:15]1[C:23]([O:24][CH3:25])=[CH:22][C:18]([C:19]([OH:21])=O)=[C:17]([N+:26]([O-:28])=[O:27])[CH:16]=1)(=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.S(Cl)(Cl)=O.[N:33]1[C:42]2[C:37](=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:36]([N:43]2[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]2)=[N:35][CH:34]=1>C1C=CC=CC=1>[CH2:6]([O:14][C:15]1[C:23]([O:24][CH3:25])=[CH:22][C:18]([C:19]([N:46]2[CH2:47][CH2:48][N:43]([C:36]3[C:37]4[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=4)[N:33]=[CH:34][N:35]=3)[CH2:44][CH2:45]2)=[O:21])=[C:17]([N+:26]([O-:28])=[O:27])[CH:16]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 18585334-Piperazin-1-ylquinazolineHCID 594400844-Benzoyloxy-5-methoxy-2-nitro benzoic acid

Produkt 1

HCID 66882459[4-(Benzyloxy)-5-methoxy-2-nitrophenyl][4-(4-quinazolinyl)piperazino]methanoneAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

DMF was added to a stirred suspension of 4-benzoyloxy-5-methoxy-2-nitro benzoic acid (6) (0:500 mg, 1.65 mmol) and thionyl chloride (3 ml) in dry benzene (30 ml) and the stirring was continued for 6 h. The benzene was evaporated in vacuum and the resultant oil dissolved in dry THF (50 ml) and added dropwise over a period of 1 h to a stirred suspension of (4-quinazolinyl)piperazine (350 mg, 1.65 mmol) triethyl amine (5 ml). After the completion of addition, the reaction mixture was brought to ambient temperature and stirred for an additional hour. The THF was evaporated in vacuum and the aqueous layer was washed with ethyl acetate. The aqueous phase was then adjusted to pH 3 using 6 N HCl and extracted with ethyl acetate and washed with brine, dried over Na2SO4 and evaporated in vacuum to afford the crude product of (7d), (700 mg in 84% yield). 1H NMR (CDCl3) δ 3.15-3.30 (m, 4H), 3.65-3.75 (m, 4H), 3.95 (s, 3H), 5.20 (s, 2H), 6.45-6.55 (t, 1H) 6.70 (s, 1H), 7.30-7.50 (m, 5H), 7.55-7.65 (t, 1H), 7.65 (s, 1H), 7.70-7.90 (m, 2H), 7.85-7.95 (m, 2H); FABMS: 500 (M+H)+.

Aufarbeitung

  1. customThe benzene was evaporated in vacuum
  2. dissolutionthe resultant oil dissolved in dry THF (50 ml)
  3. additionAfter the completion of addition
  4. customwas brought to ambient temperature
  5. customThe THF was evaporated in vacuum
  6. washthe aqueous layer was washed with ethyl acetate
  7. extractionextracted with ethyl acetate
  8. washwashed with brine
  9. dry with materialdried over Na2SO4
  10. customevaporated in vacuum

Quellen und Nachweise

ORD-Eintrag
ord-fa095f970c4540d4bbfa1d41e0941ca7
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309726B2

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