Benzoic Acid → 5-methyl-6-(2-phenyl-benzoxazol-6-yl)-4,5-dihydro-2H-pyridazin-3-one

HRID 1619968Notes

Reaction equation

HRID 1619968 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][C:3]=1[OH:16].[C:17](O)(=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClC(Cl)(Cl)C#N>C(#N)C>[CH3:15][CH:9]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]3[N:1]=[C:17]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[O:16][C:3]=3[CH:4]=2)=[N:13][NH:12][C:11](=[O:14])[CH2:10]1

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 11011TrichloroacetonitrileHCID 11776TriphenylphosphineHCID 179934936-(4-amino-3-hydroxy-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one

Product 1

HCID 674626375-methyl-6-(2-phenyl-benzoxazol-6-yl)-4,5-dihydro-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
120 °C

Procedure

219 mg (1 mmol) 6-(4-amino-3-hydroxy-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one, 122 mg (1 mmol) benzoic acid, 1.7 g (3 mmol) polymer-bound triphenylphosphine, 289 mg (2 mmol) trichloroacetonitrile and 7.5 ml acetonitrile are placed in a microwave vial and heated to 120° C. for 15 min at 200 W. The resin is filtered off and washed with methanol as well as acetonitrile. The solv. is eliminated by rotary evaporation i.V. and the residue is purified by RP-HPLC.

Workup

  1. filtrationThe resin is filtered off
  2. washwashed with methanol as well as acetonitrile
  3. customand the residue is purified by RP-HPLC

Sources & evidence

ORD record
ord-9e72acad523f46b080d0b437e1780aec
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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