Dimethyl Sulfoxide → HCID 16066664, Verbindung

HRID 1896201Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1896201
Cl[C:2]1[N:3]=[C:4]([NH:18][C:19]2[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]=2)[C:5]2[N:10]([CH2:11][CH2:12][O:13][CH2:14][CH3:15])[N:9]=[C:8]([CH2:16][CH3:17])[C:6]=2[N:7]=1.[NH:26]1[CH2:34][CH2:33][CH:29]([C:30]([OH:32])=[O:31])[CH2:28][CH2:27]1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>C(OCC)(=O)C.O>[CH2:14]([O:13][CH2:12][CH2:11][N:10]1[C:5]2[C:4]([NH:18][C:19]3[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][N:20]=3)=[N:3][C:2]([N:26]3[CH2:34][CH2:33][CH:29]([C:30]([OH:32])=[O:31])[CH2:28][CH2:27]3)=[N:7][C:6]=2[C:8]([CH2:16][CH3:17])=[N:9]1)[CH3:15]

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 37734-Piperidinecarboxylic acidHCID 10796Cesium carbonateHCID 16222003HCID 16222003, Verbindung

Produkt 1

HCID 16066664HCID 16066664, VerbindungAusbeute 7,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

A mixture of N-[5-chloro-1-(2-ethoxyethyl)-3-ethyl-1H-pyrazolo[4,3-d]pyrimidin-7-yl]-4-methylpyridin-2-ylamine from step 5 (5.42 g, 166 mmol), isonipecotic acid (85.9 g, 665 mmol), cesium carbonate (162 g, 498 mmol), and DMSO (55 mL) was heated, with stirring, at 125° C. After 20 h, the mixture was cooled to 20° C. and water (165 mL) was added. The mixture was stirred for 15 min and was then treated with ethyl acetate (55 mL). The layers were separated and the aqueous was treated with another portion of ethyl acetate (55 mL). The layers were separated again and the aqueous layer was taken to pH ˜5 using 6 M HCl. After stirring for 1 hour, the resulting solid was filtered, washed with water (20 mL) and dried in vacuuo, to give 5.5 g of the title compound. 1H NMR (400 MHz, DMSO-d6): 1.10 (t, 3 H), 1.30 (t, 3 H), 1.49-1.60 (m, 2 H), 1.84-1.95 (m, 2 H), 2.32-2.36 (m, 3 H), 2.52-2.57 (m, 1 H), 2.78 (q, 2 H), 2.99-3.08 (m, 2 H), 3.52 (q, 2 H), 3.78 (t, 2 H), 4.45-4.53 (m, 2 H), 4.56-4.64 (m, 2 H), 6.91 (d, 1 H), 8.05 (s, 1 H), 8.18 (d, 1 H), 9.63 (s, 1 H), 12.18 (s, 1 H). LCMS m/z 454.

Aufarbeitung

  1. temperaturewas heated
  2. temperaturethe mixture was cooled to 20° C.
  3. stirringThe mixture was stirred for 15 min
  4. customThe layers were separated
  5. additionthe aqueous was treated with another portion of ethyl acetate (55 mL)
  6. customThe layers were separated again
  7. stirringAfter stirring for 1 hour
  8. filtrationthe resulting solid was filtered
  9. washwashed with water (20 mL)
  10. customdried in vacuuo

Quellen und Nachweise

ORD-Eintrag
ord-c7e7fae5a23443c3af97eb598edfc341
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518956B2

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