N,N-Dimethylglycine → 1-[4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidino]-2-(dimethylamino)-1-ethanone
Reaction equation
Cl.Cl.[I:3][C:4]1[C:12]2[C:7](=[N:8][CH:9]=[N:10][C:11]=2[NH2:13])[N:6]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[N:5]=1.[CH3:20][N:21]([CH3:26])[CH2:22][C:23](O)=[O:24].ON1C2N=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(NC(C)C)C>ClCCl>[NH2:13][C:11]1[N:10]=[CH:9][N:8]=[C:7]2[N:6]([CH:14]3[CH2:19][CH2:18][N:17]([C:23](=[O:24])[CH2:22][N:21]([CH3:26])[CH3:20])[CH2:16][CH2:15]3)[N:5]=[C:4]([I:3])[C:12]=12Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
3-iodo-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine dihydrochloride salt (3 g, 7.19 mmol) was suspended in dichloromethane (350 mL) then N,N-dimethyl glycine (1.02 g, 9.88 mmol), 1-hydroxy-7-azabenzotriazole (1.08 g, 7.91 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.89 g, 9.89 mmol), and N-ethyl-N-isopropylamine (5.06 g, 39.2 mmol) were added over 4 days. The reaction was diluted with dichloromethane (300 mL) then washed with water (150 mL) and brine (150 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 1-[4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidino]-2-(dimethylamino)-1-ethanone as a tan solid (2.74 g, 6.39 mmol).
Workup
- washthen washed with water (150 mL) and brine (150 mL)
- dry with materialThe organic layer was dried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-69c521db659949ce8dd239751c7cc2fa
- Source dataset
- uspto-grants-2005_07
- Patent number
- US06921763B2
Reaction notes
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