Potassium Carbonate → 8-Nitro-2-(4-phenoxyphenyl)-5,6-dihydro-4H-benzo[f]pyrazolo[1,5-a][1,3]diazepine-3-carboxamide

HRID 64345Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 64345
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:9][CH:8]=2)[C:3]=1[C:20]([NH2:22])=[O:21].C([O-])([O-])=O.[K+].[K+].F[C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][C:31]=1[CH2:39][CH2:40]O>CN(C=O)C>[N+:36]([C:33]1[CH:34]=[CH:35][C:30]2[N:6]3[N:5]=[C:4]([C:7]4[CH:8]=[CH:9][C:10]([O:13][C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=5)=[CH:11][CH:12]=4)[C:3]([C:20]([NH2:22])=[O:21])=[C:2]3[NH:1][CH2:40][CH2:39][C:31]=2[CH:32]=1)([O-:38])=[O:37]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 248284032-(2-Fluoro-5-nitrophenyl)ethanolHCID 178513497HCID 178513497, Verbindung

Produkt 1

HCID 1369280848-Nitro-2-(4-phenoxyphenyl)-5,6-dihydro-4H-benzo[f]pyrazolo[1,5-a][1,3]diazepine-3-carboxamideAusbeute 11,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 5-amino-3-(4-phenoxyphenyl)-1H-pyrazole-4-carboxamide (30 mg, 0.10 mmol) in DMF (5.0 mL) was added K2CO3 (28 mg, 0.20 mmol), followed by 2-(2-fluoro-5-nitrophenyl)ethanol (37 mg, 0.20 mmol). The mixture was warmed to 80° C. stirred for about 16 hr. After cooling down to RT, the mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate (15 mL) and water (15 mL), the aqueous was extracted with ethyl acetate (3×10 mL). The combined organic phases were washed brine (10 mL), dried over Na2SO4, filtered, concentrated and purified by Pre-TLC (DCM/CH3OH=20/1) to afford the product about 5.0 mg (11.1%). 1H NMR (400 MHz, DMSO-d6) δ 8.35 (t, J=4.0 Hz, 1 H), 8.28 (d, J=2.8 Hz, 1 H), 8.22 (dd, J=2.8, 9.2 Hz, 1 H), 8.12 (d, J=9.2 Hz, 1 H), 7.64-7.60 (m, 2 H), 7.45-7.41 (m, 2 H), 7.22-7.17 (m, 1 H), 7.14-7.09 (m, 4 H), 3.72-3.65 (m, 2 H), 3.29-3.24 (m, 2 H). MS (ESI) m/e [M+1]+ 442.

Aufarbeitung

  1. temperatureAfter cooling down to RT
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate (15 mL) and water (15 mL)
  4. extractionthe aqueous was extracted with ethyl acetate (3×10 mL)
  5. washThe combined organic phases were washed brine (10 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified by Pre-TLC (DCM/CH3OH=20/1)

Quellen und Nachweise

ORD-Eintrag
ord-bb926eb098d442789877e0c2dd7d02f1
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447106B2

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