Hydrogen Peroxide → HCID 136983731, Verbindung

HRID 64285Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 64285
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[N:13]2[N:14]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]4[CH2:29][CH2:28]4)=[CH:21][CH:20]=3)[C:16]([C:17]#[N:18])=[C:12]2[NH:11][CH2:10][CH2:9]1.[OH-:30].[Na+].OO>CCO.CS(C)=O>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[N:13]2[N:14]=[C:15]([C:19]3[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH:27]4[CH2:29][CH2:28]4)=[CH:23][CH:24]=3)[C:16]([C:17]([NH2:18])=[O:30])=[C:12]2[NH:11][CH2:10][CH2:9]1

Komponenten

6

Edukt 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 1369280737-(2-Aminophenyl)-2-(4-(cyclopropylmethoxy)phenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile

Produkt 1

HCID 136983731HCID 136983731, VerbindungAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 7-(2-aminophenyl)-2-(4-(cyclopropylmethoxy)phenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carbonitrile (350 mg, 0.91 mmol) in EtOH (4 mL) and DMSO (4 mL) was added NaOH aqueous solution (5 N, 2 mL) and H2O2 (2 mL). After stirring at 60° C. for 3 hr, the mixture was partitioned between 100 mL of H2O and 100 mL of EA. The organic layer was separated from aqueous layers, washed with saturated brines (100 mL×2), dried over Na2SO4 and concentrated. The residue was purified by chromatography column on silica gel (elution with DCM/MeOH) to afford 150 mg (41%) of desired product as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 7.37 (d, J=8.8 Hz, 2H), 6.97-6.92 (m, 3H), 6.75 (br s, 1H), 6.67 (d, J=8.0 Hz, 1H), 6.49 (t, J=7.6 Hz, 1H), 6.27 (d, J=7.6 Hz, 1H), 5.58-5.54 (m, 1H), 5.16 (s, 2H), 3.83 (d, J=7.2 Hz, 2H), 3.27-3.24 (m, 1H), 3.01-2.92 (m, 1H), 2.23-2.13 (m, 1H), 2.13-2.07 (m, 1H), 1.24-1.18 (m, 1H), 0.59-0.54 (m, 2H) and 0.34-0.30 (m, 2H). MS (ESI) m/e [M+1]+ 404.0.

Aufarbeitung

  1. customthe mixture was partitioned between 100 mL of H2O and 100 mL of EA
  2. customThe organic layer was separated from aqueous layers
  3. washwashed with saturated brines (100 mL×2)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography column on silica gel (elution with DCM/MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-f9d81c347cce4837846a7a39a3ad6f9b
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447106B2

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