Isocyanatocarbonyl chloride → 8-(3,4-difluorophenyl)-7,8-dihydropyrano[3,4-e][1,3]oxazine-2,4(3H,5H)-dione
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14](=[O:15])[CH2:13][CH2:12][O:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[C:16](Cl)([N:18]=[C:19]=[O:20])=[O:17]>>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:14]3[O:15][C:19](=[O:20])[NH:18][C:16](=[O:17])[C:13]=3[CH2:12][O:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[F:8]Participants
3
Procedure
3-(3,4-difluorophenyl)dihydro-2H-pyran-4(3H)-one (Intermediate Y(2)) was reacted as described in Intermediate X(3) with carbonisocyanatidic chloride to give 8-(3,4-difluorophenyl)-7,8-dihydropyrano[3,4-e][1,3]oxazine-2,4(3H,5H)-dione (Intermediate Y(3)). LC-MS (M+H)+=282.1. 1H NMR (500 MHz, CDCl3) δ ppm 7.08-7.20 (m, 3 H) 4.67 (d, J=15.26 Hz, 1 H) 4.46 (dd, J=15.56, 2.14 Hz, 1 H) 3.98-4.10 (m, 2 H) 3.67 (br. s., 1 H).
Sources & evidence
- ORD record
- ord-a28e7ea353ad45bf92886b14a8f5d8fc
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710061B2
Reaction notes
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