Methyl chloroformate → Methyl {4,6-diamino-2-[6-fluoro-3-(2-fluorobenzyl)-1H-pyrazolo [4,3-b]pyridin-1-yl]pyrimidin-5-yl}carbamate
Reaktionsgleichung
[F:1][C:2]1[CH:3]=[C:4]2[N:10]([C:11]3[N:16]=[C:15]([NH2:17])[C:14]([NH2:18])=[C:13]([NH2:19])[N:12]=3)[N:9]=[C:8]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[C:5]2=[N:6][CH:7]=1.Cl[C:29]([O:31][CH3:32])=[O:30]>N1C=CC=CC=1>[NH2:19][C:13]1[C:14]([NH:18][C:29](=[O:30])[O:31][CH3:32])=[C:15]([NH2:17])[N:16]=[C:11]([N:10]2[C:4]3[C:5](=[N:6][CH:7]=[C:2]([F:1])[CH:3]=3)[C:8]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])=[N:9]2)[N:12]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
Under argon, 1.00 g (2.72 mmol) of the compound from example 8A was initially charged in pyridine (55 ml), the mixture was cooled to 0° C. and 228 μl (2.72 mmol) of methyl chloroformate (solution in 10 ml of dichloromethane) were then added dropwise. The reaction mixture was stirred further at RT overnight and then concentrated. The residue was triturated with ethanol and the solid was filtered off and dried at 50° C. under high vacuum. This gave 873 mg (75% of theory) of the target compound as a solid. The filtrate was re-concentrated, and preparative RP-HPLC (acetonitrile:water (+0.1% formic acid) gradient) of the residue gave a further 180 mg (16% of theory) of the target compound.
Aufarbeitung
- concentrationconcentrated
- customThe residue was triturated with ethanol
- filtrationthe solid was filtered off
- customdried at 50° C. under high vacuum
- concentrationThe filtrate was re-concentrated
- custompreparative RP-HPLC (acetonitrile:water (+0.1% formic acid) gradient) of the residue gave a further 180 mg (16% of theory) of the target compound
Quellen und Nachweise
- ORD-Eintrag
- ord-93d00c0099c14445b13de192246ab607
- Quelldatensatz
- uspto-grants-2015_07
- Patentnummer
- US09090609B2
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