Methyl chloroformate → Nelociguat

HRID 346537Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 346537
Cl.Cl.Cl.[F:4][C:5]1[CH:29]=[CH:28][CH:27]=[CH:26][C:6]=1[CH2:7][N:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]([C:17]2[N:22]=[C:21]([NH2:23])[C:20]([NH2:24])=[C:19]([NH2:25])[N:18]=2)=[N:9]1.Cl[C:31]([O:33][CH3:34])=[O:32]>N1C=CC=CC=1>[NH2:25][C:19]1[C:20]([NH:24][C:31](=[O:32])[O:33][CH3:34])=[C:21]([NH2:23])[N:22]=[C:17]([C:10]2[C:11]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[N:8]([CH2:7][C:6]3[CH:26]=[CH:27][CH:28]=[CH:29][C:5]=3[F:4])[N:9]=2)[N:18]=1

Komponenten

4

Edukt 2

HCID 6586Methyl chloroformateHCID 219348182-(1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidine-4,5,6-triamine trihydrochloride

Produkt 1

HCID 11690019Nelociguat

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

30.5 g (87.0 mmol) of 2-[1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-4,5,6-pyrimidinetriamine trihydrochloride from Example 8A are dissolved in 30 ml of pyridine. The resulting solution is cooled to 0° C. 8.22 g (87.0 mmol) of methyl chloroformate are added, and the mixture is stirred at 0° C. for a further 2 hours. It is subsequently allowed to warm to room temperature and is stirred for a further 12 hours. After concentration in vacuo, the residue is washed with water and dried. Further purification is effected by stirring in 300 ml of boiling diethyl ether. The precipitated product is filtered off with suction and dried in vacuo.

Aufarbeitung

  1. temperatureto warm to room temperature
  2. stirringis stirred for a further 12 hours
  3. concentrationAfter concentration in vacuo
  4. washthe residue is washed with water
  5. customdried
  6. customFurther purification
  7. stirringby stirring in 300 ml of boiling diethyl ether
  8. filtrationThe precipitated product is filtered off with suction
  9. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-eb9039af0a234a438b689d17ff8871c4
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173037B2

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