Ethanol → HCID 135482330, compound

HRID 1692729

Reaction equation

HRID 1692729 reaction equation
[NH2:1][C:2]1[N:6]([CH:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[N:5]=[CH:4][C:3]=1[C:12]([NH2:14])=[O:13].[Cl:15][C:16]1[CH:17]=[C:18]([CH2:22][C:23](OCC)=O)[CH:19]=[CH:20][CH:21]=1.C(O)C.[H-].[Na+]>O>[Cl:15][C:16]1[CH:17]=[C:18]([CH:19]=[CH:20][CH:21]=1)[CH2:22][C:23]1[NH:14][C:12](=[O:13])[C:3]2[CH:4]=[N:5][N:6]([CH:7]3[CH2:11][CH2:10][CH2:9][CH2:8]3)[C:2]=2[N:1]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 8063366Ethyl 2-(3-chlorophenyl)acetateHCID 117011915-amino-1-cyclopentyl-1H-pyrazole-4-carboxamide

Product 1

HCID 135482330HCID 135482330, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under argon, 180 mg (0.91 mmol) of 5-amino-1-cyclopentyl-1H-pyrazole-4-carboxamide and 575 mg (2.72 mmol; 3 equiv.) of ethyl (3-chlorophenyl)acetate are introduced into 3.5 ml of absolute ethanol. At 0° C., 127 mg of sodium hydride (60% dispersion in mineral oil; 3.18 mmol; 3.5 equiv.) are slowly added in a countercurrent of argon. The resulting mixture is slowly warmed and stirred under reflux for 18 h. The mixture is worked up by adding 50 ml of water and extracted several times with ethyl acetate. The combined organic phases are dried over sodium sulfate and concentrated in vacuo. The crude product is purified by preparative HPLC.

Workup

  1. temperatureThe resulting mixture is slowly warmed
  2. temperatureunder reflux for 18 h
  3. extractionextracted several times with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-31b26db9e03744e59abc79ad8d68d153
Source dataset
uspto-grants-2012_04
Patent number
US08158633B2

Linked notes

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