Pyridine → HCID 58788400, compound

Reaction equation

Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10]C(N)=N)=[CH:5][CH:4]=1.O=[C:15]1[N:20]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:19]2[CH:27]=[CH:28][CH:29]=[CH:30][C:18]=2[C:17](=[O:31])O1.[N:32]1C=CC=CC=1>>[F:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:15]2[N:20]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:19]3[C:18]([C:17](=[O:31])[N:32]=2)=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:5][CH:4]=1

Participants

Reactant 3

HCID 1049Pyridine

HCID 3568603ethyl (2,4-dioxo-2H-3,1-benzoxazin-1(4H)-yl)acetate

HCID 69157575HCID 69157575, compound

Product 1

HCID 58788400HCID 58788400, compoundYield 36%

Procedure

A solution of 3-(4-fluorophenyl)-propionamidine hydrochloride (Int. A108) (0.42 g, 2.05 mmol) and ethyl 2-(2,4-dioxo-4H-benzo[d][1,3]oxazin-1-yl)-acetate (0.51 g, 2.05 mmol) in pyridine (20 ml) was heated at reflux for 16 h, allowed to cool then concentrated in vacuo. The residues were chromatographed over silica eluting with ethyl acetate to yield the product as a white solid (0.26 g, 36%). 1H-NMR (CDCl3) δ 1.24 (3H, t,), 3.0 (2H, m), 3.17 (2H, m), 4.24 (2H, q), 5.29 (2H, s), 6.95 (2H, m), 7.2-7.3 (3H, m), 7.40 (1H, m), 7.67 (1H, m), 8.29 (1H, dd); MS (APCI+) found (M+1)=355; C20H19FN2O3 requires 354.