Pyrazole → HCID 59370358, compound

HRID 1848618Notes

Reaction equation

HRID 1848618 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([N:8]([C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[O:17][CH3:18])[CH3:9])=[O:7])=[CH:4][C:3]=1[C:21]1[CH:22]=[N:23][C:24](Cl)=[CH:25][C:26]=1[CH3:27].[NH:29]1[CH:33]=[CH:32][CH:31]=[N:30]1.C([O-])([O-])=O.[K+].[K+].CNCCNC>O1CCOCC1.[Cu]I>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([C:6]([N:8]([C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[O:17][CH3:18])[CH3:9])=[O:7])=[CH:4][C:3]=1[C:21]1[CH:22]=[N:23][C:24]([N:29]2[CH:33]=[CH:32][CH:31]=[N:30]2)=[CH:25][C:26]=1[CH3:27]

Participants

7

Reactant 4

HCID 1048PyrazoleHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 86642576HCID 86642576, compound

Product 1

HCID 59370358HCID 59370358, compoundYield 6.3%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 4-chloro-3-(6-chloro-4-methyl-pyridin-3-yl)-N-(2-methoxy-6-methyl-phenyl)-N-methyl-benzamide 2-31 (66.0 mg, 0.16 mmol) and pyrazole (12.9 mg, 0.19 mmol) was added to CuI (6.0 mg, 0.032 mmol), K2CO3 (43.9 mg, 0.32 mmol) and N,N′-dimethyethylenediamine (1.4 mg, 0.016 mmol) in dioxane (1 mL). The reaction vessel was sealed and heated at 130° C. for 24 hrs. The mixture was then filtered and purified by HPLC giving 4-chloro-N-(2-methoxy-6-methyl-phenyl)-N-methyl-3-(4-methyl-6-pyrazol-1-yl-pyridin 3-yl)-benzamide 25-1 (4.5 mg). MS (M+H)+: 446.8, tR=8.60 min (method 2).

Workup

  1. customThe reaction vessel was sealed
  2. filtrationThe mixture was then filtered
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-8a455e0fef3d46ac92becf2248da7131
Source dataset
uspto-grants-2015_02
Patent number
US08952161B2

Reaction notes

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