1-Hydroxybenzotriazole → 7-Benzylamino-3-ethoxycarbonyl-6-(3-methyl-4-phenylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyrimidine
Reaction equation
[CH2:1]([NH:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:13]2[N:12]=[CH:11][C:10]=1[C:23]([OH:25])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:27][CH:28]1[CH:33]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:32][CH2:31][NH:30][CH2:29]1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:1]([NH:8][C:9]1[N:14]2[N:15]=[CH:16][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:13]2[N:12]=[CH:11][C:10]=1[C:23]([N:30]1[CH2:31][CH2:32][CH:33]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:28]([CH3:27])[CH2:29]1)=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
7-Benzylamino-3-ethoxycarbonylpyrazolo[1,5-a]pyrimidine-6-carboxylic acid (0.20 g, 0.58 mmol) obtained in step 4 was dissolved in DMF (2 mL), 3-methyl-4-phenylpiperidine hydrochloride (Journal of Heterocyclic Chemistry, vol. 12, page 709, 0.15 g, 0.70 mmol), 1-hydroxybenzotriazole (0.13 g, 0.70 mmol) and 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride (0.10 g, 0.70 mmol) were added, and the mixture was stirred at room temperature for 3 hr. Saturated aqueous sodium hydrogen carbonate solution (10 mL) was added dropwise to the reaction mixture, and the precipitated solid was m collected by filtration. The obtained solid was washed with water, and dried under reduced pressure at 50° C. overnight to give the title compound (0.23 g, 81%).
Workup
- filtrationcollected by filtration
- washThe obtained solid was washed with water
- customdried under reduced pressure at 50° C. overnight
Sources & evidence
- ORD record
- ord-09dee278ffd24fd988560af43e0ca678
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08729264B2
Reaction notes
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