Methylamine → 2-(Dimethoxymethyl)-5,6,7,8-tetrahydro-n-methyl-1,8-naphthyridine-3-methanamine
Reaction equation
CN.[CH3:3][O:4][CH:5]([O:18][CH3:19])[C:6]1[C:15]([CH:16]=O)=[CH:14][C:13]2[CH2:12][CH2:11][CH2:10][NH:9][C:8]=2[N:7]=1.Cl.CN.[C:23]([BH3-])#[N:24].[Na+]>CO.O>[CH3:3][O:4][CH:5]([O:18][CH3:19])[C:6]1[C:15]([CH2:16][NH:24][CH3:23])=[CH:14][C:13]2[CH2:12][CH2:11][CH2:10][NH:9][C:8]=2[N:7]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 70 °C
Procedure
A solution of methylamine in MeOH (8M, 1.06 ml, 8.46 mmol) was added to a mixture of 2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridine-3-carbaldehyde (intermediate 41, 1.0 g, 4.23 mmol) and methylamine hydrochloride (0.57 g, 8.46 mmol), in MeOH (20 ml) at room temperature. Sodium cyanoborohydride (1.06 g, 16.93 mmol) was then added and the reaction mixture heated at 70° C. for 2 h. Water was added to the cooled reaction mixture and the volume reduced under vacuum. The remaining predominantly aqueous phase was then extracted with DCM (3×), dried over Na2SO4 and evaporated to give the title compound. (UPLC-MS 7) tR 0.33; ESI-MS 252.2 [M+H]+.
Workup
- extractionThe remaining predominantly aqueous phase was then extracted with DCM (3×)
- dry with materialdried over Na2SO4
- customevaporated
Sources & evidence
- ORD record
- ord-4c24c3ae662444ee8bdc22334d0c17c8
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266883B2
Reaction notes
Loading…