Dichloromethane → HCID 67816532, compound

HRID 1772381Notes

Reaction equation

HRID 1772381 reaction equation
C([O:4][CH2:5][C:6]1[O:10][N:9]=[C:8]([CH3:11])[C:7]=1[C:12]1[C:13]([C:18](=[O:26])[C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[N:14][N:15]([CH3:17])[CH:16]=1)(=O)C.[OH-].[Na+].C(Cl)Cl>C1COCC1>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]([C:13]2[C:12]([C:7]3[C:8]([CH3:11])=[N:9][O:10][C:6]=3[CH2:5][OH:4])=[CH:16][N:15]([CH3:17])[N:14]=2)=[O:26])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 67816276HCID 67816276, compound

Product 1

HCID 67816532HCID 67816532, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of (4-(3-(4-chlorobenzoyl)-1-methyl-1H-pyrazol-4-yl)-3-methylisoxazol-5-yl)methyl acetate (0.3 g, 0.8 mmol) in THF (10 mL), was added NaOH solution (5 mL, 1 N in water). The mixture was stirred for 2 hours at 55° C. After cooling to room temperature, DCM (50 mL) was added and the layers separated. The separated organic layer was dried over anhydrous sodium sulfate and concentrated to afford the titled product as a yellow oil (0.2 g, 75% yield). LC/MS m/z 331 [M+H]+; 1H NMR (300 MHz, CDCl3) δ 8.13 (d, J=9 Hz, 2H), 7.45 (d, J=9 Hz, 3H), 4.62 (s, 2H), 4.07 (s, 3H), 2.15 (s, 3H).

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe layers separated
  3. dry with materialThe separated organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7e6a52aeb4b44e299f74a1ce4e8921dc
Source dataset
uspto-grants-2016_02
Patent number
US09249161B2

Reaction notes

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