Water → HCID 17747837, compound

HRID 555956Notes

Reaction equation

HRID 555956 reaction equation
[F:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]([OH:24])([CH3:23])[CH2:19][CH:20]([CH3:22])[CH3:21])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[F:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[O:24][C:18]([CH2:19][CH:20]([CH3:21])[CH3:22])([CH3:23])[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 17747836HCID 17747836, compound

Product 1

HCID 17747837HCID 17747837, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The above product from step 2 is boiled in 150 ml of toluene with 0.2 g of p-toluenesulphonic acid on a water separator for 2 h. The mixture is washed with aqueous sodium bicarbonate solution and the organic phase is concentrated under reduced pressure. By stirring with heptane, it is possible to precipitate and remove by filtration the N-(2-acetylphenyl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide still present from the previous step. Chromatography gives 7.2 g (purity 85.1%; 63% of theory) of 2-(5-fluoro-1,3-dimethyl-1H-pyrazol-4-yl)-4-isobutyl-4-methyl-4H-3,1-benzoxazine.

Workup

  1. washThe mixture is washed with aqueous sodium bicarbonate solution
  2. concentrationthe organic phase is concentrated under reduced pressure
  3. customto precipitate
  4. customremove by filtration the N-(2-acetylphenyl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide

Sources & evidence

ORD record
ord-7bf960937c0d410cac83907d809ce0e3
Source dataset
uspto-grants-2011_11
Patent number
US08053572B2

Reaction notes

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