Pyridine → HCID 58788400, compound

HRID 2374745Notes

Reaction equation

HRID 2374745 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

4

Reactant 3

HCID 1049PyridineHCID 3568603ethyl (2,4-dioxo-2H-3,1-benzoxazin-1(4H)-yl)acetateHCID 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.

Workup

  1. temperatureat reflux for 16 h
  2. temperatureto cool
  3. concentrationthen concentrated in vacuo
  4. customThe residues were chromatographed over silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-35f77dc5be6a452e9ebbcd797e6842a6
Source dataset
uspto-grants-2008_12
Patent number
US07462620B2

Reaction notes

Loading…