Benzaldehyde → 6-Amino-3-methyl-1,4-diphenyl-1,4-dihydropyrano(2,3-c)pyrazole-5-carbonitrile

HRID 531189

Reaktionsgleichung

Reaktionsgleichung von HRID 531189
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](#[N:13])[CH2:10][C:11]#[N:12].[CH3:14][C:15]1[CH2:19][C:18](=[O:20])[N:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:16]=1.[O-]S([O-])(=O)=O.[Na+].[Na+].CC[C@@H]1[C@@H]2C[C@@H]([C@H](O)C3C4C=C(OCC)C=CC=4N=CC=3)N(CC2)C1.Cl>C(Cl)Cl>[NH2:12][C:11]1[O:20][C:18]2[N:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:16]=[C:15]([CH3:14])[C:19]=2[CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10]=1[C:9]#[N:13]

Komponenten

7

Edukt 5

HCID 240BenzaldehydeHCID 4021Mci-186HCID 8010MalononitrileHCID 24436Sodium SulfateHCID 16219340Ethylhydrocupreine hydrochloride

Produkt 1

HCID 3268106-Amino-3-methyl-1,4-diphenyl-1,4-dihydropyrano(2,3-c)pyrazole-5-carbonitrileAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of benzaldehyde (290 μL, 2.87 mmol), malononitrile (190 mg, 2.87 mmol) and 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one (500 mg, 2.87 mmol) in anhydrous DCM (60 mL) was added anhydrous Na2SO4 (407 mg, 2.87 mmol) and ethylhydrocupreine hydrochloride (46 mg, 0.122 mmol). The reaction mixture was stirred at room temperature (25 h). After filtration and washing with DCM, the solvent was removed under reduced pressure. The crude mixture was subjected to flash column chromatography over silica gel (hexanes:ethyl acetate; 1:1) to give 6-amino-3-methyl-1,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (270 mg, 0.822 mmol, 29%) as white solid. 1H-NMR (400 MHz) CDCl3: 7.69-7.66 (d, 2H), 7.50-7.46 (t, 2H), 7.39-7.26 (m, 6H), 4.68 (s, 1H), 4.67 (s, 2H), 1.91 (s, 3H), 13C-NMR (100 MHz) CDCl3: 158.1, 146.4, 143.8, 141.9, 137.5, 129.2, 128.8, 127.8, 127.5, 126.7, 121.2, 119.0, 98.3, 64.0, 37.4, 12.8; LC/MS-MS: 329.1→263.1 m/z; GS1 and GS2 at 30, DP=56, CE=31, CXP=18, tR=4.18 min.

Aufarbeitung

  1. filtrationAfter filtration
  2. washwashing with DCM
  3. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-5d5434c2e6ba43a2b4af83306eda635e
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09353121B2

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