Reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][CH2:11][C:12]3[C:17]([CH3:18])=[CH:16][CH:15]=[CH:14][C:13]=3[CH2:19][CH3:20])=[CH:8][C:7]([C:21]([OH:23])=O)=[CH:6][N:5]2[C:24]=1[CH3:25].[B-](F)(F)(F)F.[CH3:31][N:32](C(ON1N=NC2C1=CC=CC=2)=[N+](C)C)C.CN>C(Cl)Cl>[CH2:19]([C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([CH3:18])[C:12]=1[CH2:11][NH:10][C:9]1[C:4]2[N:5]([C:24]([CH3:25])=[C:2]([CH3:1])[N:3]=2)[CH:6]=[C:7]([C:21]([NH:32][CH3:31])=[O:23])[CH:8]=1)[CH3:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2,3-Dimethyl-8-(2-ethyl-6-methylbenzylamino)-imidazo[1,2-a]pyridine-6-carboxylic acid (0.15 g, 0.44 mmol) and o-Benzotriazol-1-yl-N,N,N′,N′-Tetramethyluronium tetrafluoroborate (TBTU) (0.14 g, 0.44 mmol) were added to methylene chloride (10 ml) and the reaction mixture was stirred at room temperature for 15 min. Methylamine (0.1 g, 3.2 mmol) was added and the reaction mixture was stirred at ambient temperature for 1.5 h. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using ethylacetate:methylene chloride (1:1) as eluent. The yield was treated with diethyl ether to give 40 mg (26%) of the desired product.
Workup
- stirringthe reaction mixture was stirred at ambient temperature for 1.5 h
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by column chromatography on silica gel
- additionThe yield was treated with diethyl ether
Sources & evidence
- ORD record
- ord-21e4605fc6fd4ff89efa148354f82356
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06313137B1
Linked notes
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