Triethylamine → 5-Bromo-3-(4-(4-methylpiperazin-1-yl)phenylamino)picolinamide
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4](F)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[CH3:11][N:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=2)[CH2:14][CH2:13]1.C(N(CC)CC)C.CC(C)([O-:35])C.[Na+]>C(O)(C)(C)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:22][C:21]2[CH:23]=[CH:24][C:18]([N:15]3[CH2:14][CH2:13][N:12]([CH3:11])[CH2:17][CH2:16]3)=[CH:19][CH:20]=2)[C:5]([C:8]([NH2:9])=[O:35])=[N:6][CH:7]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A solution of EXAMPLE 49A (1.8 g, 8.96 mmol) and 4-(4-methylpiperazin-1-yl)aniline (1.713 g, 8.96 mmol) in t-butanol (10 mL) was treated with triethylamine (1.87 mL, 13.43 mmol) was subjected to microwave irradiation (Biotage, Initiator) at 190° C. for 1.5 hours. The reaction mixture was concentrated and purified on silica gel with 0-10% methanol in dichloromethane. The collected material was taken into t-butanol (5 mL), treated with sodium t-butoxide (1.73 g, 18 mmol), and the reaction mixture was stirred at 90° C. for 2 hours. The mixture was concentrated and purified on silica gel with 3-13% methanol in dichloromethane to afford the title compound.
Workup
- customwas subjected to microwave irradiation (Biotage, Initiator) at 190° C. for 1.5 hours
- concentrationThe reaction mixture was concentrated
- custompurified on silica gel with 0-10% methanol in dichloromethane
- concentrationThe mixture was concentrated
- custompurified on silica gel with 3-13% methanol in dichloromethane
Sources & evidence
- ORD record
- ord-74cd8cbcb07946b9bbf0b02792c30065
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08859546B2
Reaction notes
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