Pyrazole → HCID 57889906, compound

HRID 1820193Notes

Reaction equation

HRID 1820193 reaction equation
Cl[CH2:2][C:3]([NH:5][C@H:6]([CH:22]([CH3:24])[CH3:23])[C:7]([N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)=[O:8])=[O:4].[NH:25]1[CH:29]=[CH:28][CH:27]=[N:26]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH:12]2[CH2:13][CH2:14][N:9]([C:7](=[O:8])[C@H:6]([NH:5][C:3](=[O:4])[CH2:2][N:25]3[CH:29]=[CH:28][CH:27]=[N:26]3)[CH:22]([CH3:24])[CH3:23])[CH2:10][CH2:11]2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 57889186HCID 57889186, compound

Product 1

HCID 57889906HCID 57889906, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
75 °C

Procedure

In a sealed vial were added consecutively (R)-2-chloro-N-(1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methyl-1-oxobutan-2-yl)acetamide (31.4 mg, 0.085 mmol), pyrazole (11.5 mg, 0.17 mmol), K2CO3 (35.2 mg, 0.26 mmol) and acetonitrile (0.4 mL). The reaction mixture was then heated at 75° C. for 36 h, cooled to rt., and the solids were filtered. The filtrate was concentrated and purified by preparative HPLC to provide Example 290, (R)—N-(1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methyl-1-oxobutan-2-yl)-2-(1H-pyrazol-1-yl)acetamide (32 mg, 94% yield) as a white solid. MS found: 403.3 (M+H).

Workup

  1. temperaturecooled to rt
  2. filtration, and the solids were filtered
  3. concentrationThe filtrate was concentrated
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-1a7c5f0a14954f809ce81b209a36b3d0
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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