Methyl chloroformate → Vericiguat Impurity 100

HRID 1875457Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1875457
[F:1][C:2]1[CH:26]=[CH:25][CH:24]=[CH:23][C:3]=1[CH2:4][C:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[N:7]([C:14]2[N:19]=[C:18]([NH2:20])[C:17]([NH2:21])=[C:16]([NH2:22])[N:15]=2)[N:6]=1.Cl[C:28]([O:30][CH3:31])=[O:29]>N1C=CC=CC=1>[CH3:31][O:30][C:28](=[O:29])[NH:21][C:17]1[C:16]([NH2:22])=[N:15][C:14]([N:7]2[C:8]3[C:9](=[N:10][CH:11]=[CH:12][CH:13]=3)[C:5]([CH2:4][C:3]3[CH:23]=[CH:24][CH:25]=[CH:26][C:2]=3[F:1])=[N:6]2)=[N:19][C:18]=1[NH2:20]

Komponenten

4

Edukt 2

HCID 6586Methyl chloroformateHCID 24794429HCID 24794429, Verbindung

Produkt 1

HCID 24794430Vericiguat Impurity 100

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

200 mg (0.57 mmol) of 2-[3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]pyrimidine-4,5,6-triamine from example 8 are dissolved in 10 ml of pyridine. The solution is cooled to 0° C., and 81 mg (0.86 mmol) of methyl chloroformate are added. The reaction mixture is stirred at RT overnight and then concentrated in vacuo, mixed with ethyl acetate and washed twice with water and with saturated sodium chloride solution. The organic phase is dried over sodium sulfate and concentrated in vacuo. The residue is purified by preparative HPLC to result in 125 mg (54% of theory) of the title compound as a pale beige solid.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. additionmixed with ethyl acetate
  3. washwashed twice with water and with saturated sodium chloride solution
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d6e0e2c53cee4919a0bfd3950ffb96ee
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08309551B2

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