HCID 3730890, compound → HCID 86668513, compound

HRID 2047249Notes

Reaction equation

HRID 2047249 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([C:18]([C:23](=O)[C:24]([F:27])([F:26])[F:25])=[CH:19][N:20](C)C)[O:11][N:10]=1.[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[C:40]([C:41]([O:43][CH3:44])=[O:42])=[C:39]([NH:45]N)[O:38][N:37]=2)=[CH:32][CH:31]=1>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:13]([C:14]([O:16][CH3:17])=[O:15])=[C:12]([C:18]2[CH:19]=[N:20][N:45]([C:39]3[O:38][N:37]=[C:36]([C:33]4[CH:32]=[CH:31][C:30]([Cl:29])=[CH:35][CH:34]=4)[C:40]=3[C:41]([O:43][CH3:44])=[O:42])[C:23]=2[C:24]([F:25])([F:26])[F:27])[O:11][N:10]=1

Participants

4

Reactant 2

HCID 3730890HCID 3730890, compoundHCID 68153105HCID 68153105, compound

Product 1

HCID 86668513HCID 86668513, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

The mixture of methyl 3-(2-chloro-6-fluorophenyl)-5-(1-(dimethylamino)-4,4,4-trifluoro-3-oxobut-1-en-2-yl)isoxazole-4-carboxylate (157 mg, 0.37 mmol) and methyl 3-(4-chlorophenyl)-5-hydrazinoisoxazole-4-carboxylate (0.1 g, 0.37 mmol) in ethanol (1 mL) was heated at 60° C. for 5 h, the solution was evaporated and the product was crystallized from methanol to give 86 mg (37%) of example 131. 1H NMR (DMSO-D6, CCl4): 3.69 (3H, s, OCH3), 3.71 (3H, s, OCH3), 7.35 (1H, dd, CH-arom.), 7.47 (1H, d, CH-arom.), 7.57 (2H, AB-syst., CH-arom.), 7.63 (1H, m, CH-arom.), 7.84 (2H, AB-syst., CH-arom.), 8.74 (1H, s, CH pyrazol.).

Workup

  1. customthe solution was evaporated
  2. customthe product was crystallized from methanol

Sources & evidence

ORD record
ord-71bdc404155943059e63d2fb11e13199
Source dataset
uspto-grants-2013_11
Patent number
US08592456B2

Reaction notes

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