Hydrochloric Acid → Methyl-(6-morpholin-4-yl-4-o-tolyl-pyridin-3-yl)-amine
Reaction equation
[N:1]1([C:7]2[N:12]=[CH:11][C:10]([NH2:13])=[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH3:20])[CH:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.[OH-].[Na+].[CH:30](OC)(OC)OC>FC(F)(F)C(O)=O.O1CCCC1>[CH3:30][NH:13][C:10]1[CH:11]=[N:12][C:7]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:8][C:9]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
A solution of 2.24 g (8.3 mmol) 6-morpholin-4-yl-4-o-tolyl-pyridin-3-ylamine in 17 ml trimethyl orthoformate and 3 drops trifluoroacetic acid was heated for 2 h at 130° C. The reaction mixture was evaporated and dried in vacuo for 30 min. The residual oil was dissolved in 5 ml tetrahydrofuran and was added dropwise under ice cooling to 630 mg (16.6 mmol) lithium aluminum hydride in 20 ml tetrahydrofuran. The reaction mixture was stirred for 1h at room temperature, cooled to 0° C. again and acidified (pH 1-2) by addition of 28% hydrochloric acid solution. After stirring for 5 min, 28% sodium hydroxide solution was added to reach pH 10. The solution was filtered over celite, evaporated and purified by flash chromatography to give 1.56 g (66%) of the title compound as a white foam.
Workup
- customThe reaction mixture was evaporated
- customdried in vacuo for 30 min
- dissolutionThe residual oil was dissolved in 5 ml tetrahydrofuran
- filtrationThe solution was filtered over celite
- customevaporated
- custompurified by flash chromatography
Sources & evidence
- ORD record
- ord-3d3d00ed74e749569a2c67c4232aa575
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06897226B2
Reaction notes
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