Acetic Acid → HCID 71293376, compound

HRID 1619972Notes

Reaction equation

HRID 1619972 reaction equation
O[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]([CH3:14])[CH:12]([CH2:15][CH2:16][CH3:17])[C:11](=[O:18])[NH:10][N:9]=2)[CH:5]=[CH:4][C:3]=1[NH:19][C:20]([C:22]1[N:23]([CH3:27])[CH:24]=[CH:25][CH:26]=1)=[O:21].C(O)(=O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[CH3:14][C@@H:13]1[C:8]([C:6]2[CH:5]=[CH:4][C:3]3[N:19]=[C:20]([C:22]4[N:23]([CH3:27])[CH:24]=[CH:25][CH:26]=4)[O:21][C:2]=3[CH:7]=2)=[N:9][NH:10][C:11](=[O:18])[C@H:12]1[CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 521998p-Toluenesulfonic acid monohydrateHCID 67466941HCID 67466941, compound

Product 1

HCID 71293376HCID 71293376, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
200 °C

Procedure

150 mg (407 mmol) 1-methyl-1H-pyrrole-2-carboxylic acid[2-hydroxy-4-(4-methyl-6-oxo-5-propyl-1,4,5,6-tetrahydro-pyridazin-3-yl)-phenyl]-amide are placed in 5 mL dioxane. 300 μL (5.19 mmol) acetic acid and 140 mg (814 μmol) p-toluenesulphonic acid monohydrate are added and the mixture is stirred for 60 min in the microwave at 200° C. The reaction mixture is extracted successively with 10% sodium carbonate solution, 1% acetic acid, 10% sodium carbonate solution and saline solution. Then the solv. of the organic phase is eliminated i.V. and the residue is purified through silica gel. (Cyclohexane/EA) The solv. of the corresponding fractions is eliminated i.V. and the residue is crystallised with diethyl ether/petroleum ether.

Workup

  1. extractionThe reaction mixture is extracted successively with 10% sodium carbonate solution, 1% acetic acid, 10% sodium carbonate solution and saline solution
  2. customand the residue is purified through silica gel
  3. customand the residue is crystallised with diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-d0ee0441649649f2b63601de02c77322
Source dataset
uspto-grants-2014_07
Patent number
US08772323B2

Reaction notes

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