Succinic anhydride → HCID 131723412, compound

HRID 861076Notes

Reaction equation

HRID 861076 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[C:11]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[NH:10][N:9]=2)=[CH:4][CH:3]=1.[C:25]1(=[O:31])[O:30][C:28](=[O:29])[CH2:27][CH2:26]1>CN(C)C1C=CN=CC=1>[OH2:29].[OH2:29].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][N:10]=[C:11]([N:19]3[CH2:20][CH2:21][N:22]([C:25](=[O:31])[CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH2:23][CH2:24]3)[C:12]=2[C:13]2[CH:14]=[CH:15][N:16]=[CH:17][CH:18]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 178478002HCID 178478002, compound

Product 1

HCID 131723412HCID 131723412, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A solution of 3-(4-chlorophenyl)-4-(4-pyridyl)-5-(4-piperzinyl)pyrazole (200 mg; 0.54 mmol; prepared as set forth in Example A-169), succinic anhydride (60 mg, 0.55 mmol) and 4-dimethylaminopyridine (5 mg) was stirred at room temperature for 24 hours. The solvent was removed in vacuo and the residue treated with methanol and water (1:1). The resultant crystalline solid was filtered and air dried to give 170 mg (58%) of 4-[5-(4-chlorophenyl)-4-(4-pyridinyl)-1H-pyrazol-3-yl]-γ-oxo-1-piperazinebutanoic acid, dihydrate, m. p. 281–283° C. (dec.). Anal. Calc'd. for C22H22ClN5O3.2H2O: C, 55.52; H, 5.51; N, 14.72. Found: C, 55.11; H, 5.20; N, 14.44.

Workup

  1. customprepared
  2. customThe solvent was removed in vacuo
  3. additionthe residue treated with methanol and water (1:1)
  4. filtrationThe resultant crystalline solid was filtered
  5. customair dried

Sources & evidence

ORD record
ord-0ce1129cf9d74cf3a36fb07d9aa69c64
Source dataset
uspto-grants-2006_12
Patent number
US07153959B2

Reaction notes

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