N-[4-iodo-6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-2,2-dimethyl-propionamide → 4-Iodo-6-(4-methyl-piperazin-1-yl)-pyridin-3-ylamine
Reaction equation
[I:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[N:5]=[CH:4][C:3]=1[NH:15]C(=O)C(C)(C)C>Cl>[I:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[N:5]=[CH:4][C:3]=1[NH2:15]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 2.20 g (5.47 mmol) N-[4-iodo-6-(4-methyl-piperazin-1-yl)-pyridin-3-yl]-2,2-dimethyl-propionamide (synthesis described in DE10008042) in 50 ml 3 N hydrochloric acid was stirred for 18 h at 100° C. After cooling to 0° C. the reaction mixture was washed twice with ether (50 ml). The aqueous phase was treated with 50 ml dichloromethane and basified with a 1 M solution of sodium carbonate. The organic phase was separated and the aqueous phase was extracted four times with 50 ml dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated in vacuo to give 1.60 g (92%) of the title compound as an off-white solid.
Workup
- temperatureAfter cooling to 0° C. the reaction mixture
- washwas washed twice with ether (50 ml)
- additionThe aqueous phase was treated with 50 ml dichloromethane
- customThe organic phase was separated
- extractionthe aqueous phase was extracted four times with 50 ml dichloromethane
- dry with materialThe combined organic layers were dried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-65ba94ea9e7c4e7bac31fda44fcf68c0
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07211579B2
Reaction notes
Loading…