Methanol → (Racemic) 1-(8-((5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)carbamoyl)-2-(dimethoxymethyl)-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)ethyl methanesulfonate
Reaction equation
[C:1]([C:3]1[C:4]([NH:30][CH2:31][CH2:32][O:33][CH3:34])=[CH:5][C:6]([NH:9][C:10]([N:12]2[C:21]3[C:16](=[CH:17][C:18]([CH:27]([OH:29])[CH3:28])=[C:19]([CH:22]([O:25][CH3:26])[O:23][CH3:24])[N:20]=3)[CH2:15][CH2:14][CH2:13]2)=[O:11])=[N:7][CH:8]=1)#[N:2].CCN(CC)CC.[CH3:42][S:43](Cl)(=[O:45])=[O:44].CO>C(Cl)Cl.CN(C=O)C>[CH3:42][S:43]([O:29][CH:27]([C:18]1[C:19]([CH:22]([O:25][CH3:26])[O:23][CH3:24])=[N:20][C:21]2[N:12]([C:10](=[O:11])[NH:9][C:6]3[CH:5]=[C:4]([NH:30][CH2:31][CH2:32][O:33][CH3:34])[C:3]([C:1]#[N:2])=[CH:8][N:7]=3)[CH2:13][CH2:14][CH2:15][C:16]=2[CH:17]=1)[CH3:28])(=[O:45])=[O:44]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a suspension of (racemic) N-(5-cyano-4-((2-methoxyethyl)amino)pyridin-2-yl)-7-(dimethoxymethyl)-6-(1-hydroxyethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 183, 198 mg, 0.421 mmol) and NEt3 (80 μl, 0.574 mmol) in DCM (8 ml) and DMF (0.5 ml) at 0° C. was added a solution of methanesulfonyl chloride (40 μl, 0.513 mmol) and the slurry was continued to stir at 0° C. for 4 h, after which it was directly used in the next step. (UPLC-MS 3) tR 1.15 min; ESI-MS 484.8 [M; Me-ether of MeOH quench]+.
Sources & evidence
- ORD record
- ord-8d7605649ae841c5818ac1fa9b51922d
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09266883B2
Reaction notes
Loading…