Hydrochloric Acid → Methyl[4,6-diamino-2-(1-cycloheptylmethyl-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-5-yl]-carbamate

HRID 2194469Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2194469
[CH3:1][O:2][C:3](=[O:22])[NH:4][C:5]1[C:6]([NH2:21])=[N:7][C:8]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[NH:14][N:13]=2)=[N:9][C:10]=1[NH2:11].CS(O[CH2:28][CH:29]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>CN(C)C=O>[CH3:1][O:2][C:3](=[O:22])[NH:4][C:5]1[C:10]([NH2:11])=[N:9][C:8]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:28][CH:29]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[N:13]=2)=[N:7][C:6]=1[NH2:21]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 21866479Cycloheptylmethyl methanesulfonateHCID 178502011Methyl[4,6-diamino-2-(1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-5-yl]carbamate

Produkt 1

HCID 46830429Methyl[4,6-diamino-2-(1-cycloheptylmethyl-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-5-yl]-carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

300 mg (1.0 mmol) of the compound of Example 1A and 224 mg (1.1 mmol) of cycloheptylmethyl methansulfonate (preparation: see J. Med. Chem. 2000, 43(26), 5017-5029) were initially charged in 5 ml of dimethylformamide, 354 mg (1.1 mmol) of cesium carbonate were added and the resulting mixture was stirred at RT overnight. 0.5 ml of 1N hydrochloric acid was added, and the entire solution was separated by HPLC (Method 5). The appropriate fractions were concentrated on a rotary evaporator, and the residue was dried under high vacuum. This gave 2.8 mg (0.7% of theory) of the target compound.

Aufarbeitung

  1. customthe entire solution was separated by HPLC (Method 5)
  2. concentrationThe appropriate fractions were concentrated on a rotary evaporator
  3. customthe residue was dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-1eb436a25d2b45d7a3279a2a1ecc79b6
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08334291B2

Notizen zur Reaktion

Wird geladen…