Pyridine → 5-ethyl-6-[2-(2-fluoro-4-methoxy-phenyl)-benzoxazol-6-yl]-4,5-dihydro-2H-pyridazin-3-one

HRID 1619969Notes

Reaction equation

HRID 1619969 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH2:15][CH3:16])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][C:3]=1[OH:17].[F:18][C:19]1[CH:27]=[C:26]([O:28][CH3:29])[CH:25]=[CH:24][C:20]=1[C:21](Cl)=O.N1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[CH2:15]([CH:9]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]3[N:1]=[C:21]([C:20]4[CH:24]=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:19]=4[F:18])[O:17][C:3]=3[CH:4]=2)=[N:13][NH:12][C:11](=[O:14])[CH2:10]1)[CH3:16]

Participants

6

Reactant 4

HCID 1049PyridineHCID 521998p-Toluenesulfonic acid monohydrateHCID 144847142-Fluoro-4-methoxybenzoyl chlorideHCID 674612546-(4-amino-3-hydroxy-phenyl)-5-ethyl-4,5-dihydro-2H-pyridazin-3-one

Product 1

HCID 674663155-ethyl-6-[2-(2-fluoro-4-methoxy-phenyl)-benzoxazol-6-yl]-4,5-dihydro-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

200 mg (857 μmol) 6-(4-amino-3-hydroxy-phenyl)-5-ethyl-4,5-dihydro-2H-pyridazin-3-one are refluxed together with 170 mg (901 μmol) 2-fluoro-4-methoxybenzoyl chloride, 70 mg (885 μmol) pyridine, 160 mg (841 μmol) para-toluenesulphonic acid monohydrate and 5 ml xylene for 4 h. The reaction mixture is evaporated down completely i.V. and the residue is crystallised from acetonitrile.

Workup

  1. customThe reaction mixture is evaporated down completely i.V
  2. customand the residue is crystallised from acetonitrile

Sources & evidence

ORD record
ord-81b9a590de764929b0e97cdd467f2d72
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

Loading…