Heptane → 2-Methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (2-methyl-pyridin-4-yl)-amide
Reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.C[Al](C)C.CCCCCCC.C([O:22][C:23]([C:25]1[N:26]=[C:27]([CH3:37])[S:28][C:29]=1[NH:30][C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)=O)C>O1CCOCC1>[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:23]([C:25]2[N:26]=[C:27]([CH3:37])[S:28][C:29]=2[NH:30][C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)=[O:22])[CH:5]=[CH:4][N:3]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2-methyl-pyridin-4-ylamine (0.10 g, 0.91 mmol) in dry dioxane (2.00 ml) was added to a 2N solution of trimethylaluminium in heptane (0.46 ml, 0.91 mmol). The mixture was stirred at room temperature for 1 h, then 2-methyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid ethyl ester (0.08 g, 0.30 mmol) was added and the reaction mixture was irradiated in a microwave oven at 150° C. for 15 min. The mixture was quenched with water (1.00 ml) and diluted with dichloromethane. After drying with sodium sulphate, the solvent was evaporated. The residue was purified by flash chromatography (dichloromethane/methanol) yielding the title compound (0.04 g, 41%) as a yellow solid, MS (ISP): m/e=326.1 (M+H+).
Workup
- customthe reaction mixture was irradiated in a microwave oven at 150° C. for 15 min
- customThe mixture was quenched with water (1.00 ml)
- additiondiluted with dichloromethane
- dry with materialAfter drying with sodium sulphate
- customthe solvent was evaporated
- customThe residue was purified by flash chromatography (dichloromethane/methanol)
Sources & evidence
- ORD record
- ord-1e9ff39e875b4362a4b5fa5cfca656e8
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07678815B2
Reaction notes
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