HCID 22050511, compound → HCID 54724180, compound

HRID 1831987Notes

Reaction equation

HRID 1831987 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])O[C:4](=[O:9])[CH:3]=1.[F:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[C:13]([N:18]([CH3:20])[CH3:19])[C:12]=1[NH2:21]>>[CH3:19][N:18]([CH3:20])[C:13]1[CH:14]=[C:15]([F:17])[CH:16]=[C:11]([F:10])[C:12]=1[N:21]1[C:6]([CH3:8])=[CH:7][C:2]([OH:1])=[CH:3][C:4]1=[O:9]

Participants

3

Reactant 2

HCID 22050511HCID 22050511, compoundHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54724180HCID 54724180, compoundYield 17.8%

Conditions

Temperature
160 °C

Procedure

An intimate mixture of 4-hydroxy-6-methyl-2-pyrone (1.3 g, 0.0103 mol), and 3,5-difluoro-N,N-dimethylbenzene-1,2-diamine (1.4 g, 0.008 mol) was heated at 160° C. under argon for 15 min. The dark colored reaction mixture was cooled, triturated with EtOAc (15 ml), and filtered. The solids were washed with warm EtOAc, followed by hexane and dried to give the title compound as a light blue solid (0.4 g, 14%). Analalytically pure sample was prepared by reverse-phase HPLC purification using 10-90% CH3CN/Water (30 min gradient) at a flow rate of 100 mL/min. The appropriate fractions were combined and freeze-dried to give the title compound: 1H NMR (CD3OD/400 MHz) δ 6.61 (m, 2H), 6.08 (d, 1H, J=2.0 Hz), 6.78 (d, 1H, J=2.0 Hz), 2.69 (s, 6H), and 1.94 (s, 3H); ES-HRMS m/z 281.1084 (M+H C14H15N2O2F2 requires 281.1096)

Workup

  1. temperatureThe dark colored reaction mixture was cooled
  2. customtriturated with EtOAc (15 ml)
  3. filtrationfiltered
  4. washThe solids were washed with warm EtOAc
  5. customdried

Sources & evidence

ORD record
ord-1d55e03582a5468a8925225afca39ec8
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

Loading…