Hydrochloric Acid → Methyl[4,6-diamino-2-(1-cycloheptylmethyl-1H-pyrazolo[3,4-b]pyridin-3-yl)pyrimidin-5-yl]-carbamate
Reaction equation
[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]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- customthe entire solution was separated by HPLC (Method 5)
- concentrationThe appropriate fractions were concentrated on a rotary evaporator
- customthe residue was dried under high vacuum
Sources & evidence
- ORD record
- ord-1eb436a25d2b45d7a3279a2a1ecc79b6
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08334291B2
Reaction notes
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