Ethyl 3-amino-4,4,4-trifluorocrotonate → 6-{3-[2-(ethoxycarbonyl)-1-trifluoromethyl-vinyl]ureido}-3,4-dihydro-7-fluoro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine

HRID 2253577Notes

Reaction equation

HRID 2253577 reaction equation
[NH2:1]/[C:2](/[C:9]([F:12])([F:11])[F:10])=[CH:3]\[C:4]([O:6][CH2:7][CH3:8])=[O:5].[F:13][C:14]1[C:27]([N:28]=[C:29]=[O:30])=[CH:26][C:17]2[N:18]([CH2:23][C:24]#[CH:25])[C:19](=[O:22])[CH2:20][O:21][C:16]=2[CH:15]=1>>[CH2:7]([O:6][C:4]([CH:3]=[C:2]([NH:1][C:29](=[O:30])[NH:28][C:27]1[C:14]([F:13])=[CH:15][C:16]2[O:21][CH2:20][C:19](=[O:22])[N:18]([CH2:23][C:24]#[CH:25])[C:17]=2[CH:26]=1)[C:9]([F:10])([F:11])[F:12])=[O:5])[CH3:8]

Participants

3

Reactant 2

HCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 118174397-fluoro-6-isocyanato-4-propargyl-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 543199106-{3-[2-(ethoxycarbonyl)-1-trifluoromethyl-vinyl]ureido}-3,4-dihydro-7-fluoro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine

Procedure

Analogously to the procedure described in Example 1, starting from ethyl 3-amino-4,4,4-trifluorocrotonate and 3,4-dihydro-7-fluoro-6-isocyanato-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine there is obtained 6-{3-[2-(ethoxycarbonyl)-1-trifluoromethyl-vinyl]ureido}-3,4-dihydro-7-fluoro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazine (not isolated) and, after cyclization of this benzoxazine, there is obtained 3-[3,4-dihydro-7-fluoro-3-oxo-4-(2-propynyl)-2H-1,4-benzoxazin-6-yl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, 1H-NMR (CDCl3, 60 MHz): 7.29 ppm (d, 1H), 6.99 ppm (d, 1H), 6.31 ppm (s, 1H), 4.85-4.61 ppm (m, 4H), 2.35 ppm (t, 1H): mass spectrum: m/e 383(20), M+.

Sources & evidence

ORD record
ord-09a08a36a7e8480691fd8691e6fd4dde
Source dataset
uspto-grants-1993_08
Patent number
US05232898

Reaction notes

Loading…