Ethanol → (S)-4'-fluoro-2'-methoxy-5,6-dihydrospiro[[1,3]thiazine-4,9'-xanthene]-2,7'-diamine
Reaction equation
[N:1]([C:4]1[CH:17]=[C:16]2[C:7]([O:8][C:9]3[C:10]([F:26])=[CH:11][C:12]([O:24][CH3:25])=[CH:13][C:14]=3[C@@:15]32[CH2:22][CH2:21][S:20][C:19]([NH2:23])=[N:18]3)=[CH:6][CH:5]=1)=[N+]=[N-].C(O)C>[Pd].CCOC(C)=O>[F:26][C:10]1[C:9]2[O:8][C:7]3[C:16](=[CH:17][C:4]([NH2:1])=[CH:5][CH:6]=3)[C@@:15]3([CH2:22][CH2:21][S:20][C:19]([NH2:23])=[N:18]3)[C:14]=2[CH:13]=[C:12]([O:24][CH3:25])[CH:11]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a disposable vial was charged with (S)-7′-azido-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]thiazine-4,9′-xanthen]-2-amine (170 mg, 0.458 mmol), Ethanol (1.7 ml) and EtOAc (0.8 ml). The heterogeneous mixture stirred for 5 min and palladium on carbon (48.7 mg, 0.046 mmol) was added to the vial. The mixture was hydrogenated (balloon) at room temperature overnight. The mixture was filtered through celite and concentrated. The dark residue was diluted with DCM and concentrated again. After drying in vacuo, (S)-4′-fluoro-2′-methoxy-5,6-dihydrospiro[[1,3]thiazine-4,9′-xanthene]-2,7′-diamine (120 mg, 0.347 mmol, 76% yield) was obtained as tan foam. It was used for next step without further purification.
Workup
- customat room temperature
- customovernight
- filtrationThe mixture was filtered through celite and
- concentrationconcentrated
- additionThe dark residue was diluted with DCM
- concentrationconcentrated again
- customAfter drying in vacuo
Sources & evidence
- ORD record
- ord-195f4e44ea86417ca37b55ac462a0568
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296759B2
Reaction notes
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