Ammonium Chloride → 2-{4-[2-(3,5-Dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-benzoic acid methyl ester

HRID 2096261Notes

Reaction equation

HRID 2096261 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[CH3:17][C:18]1[CH:22]=[C:21]([CH3:23])[N:20]([CH2:24][C:25](O)=[O:26])[N:19]=1.C(C1NC=CN=1)(C1NC=CN=1)=O.[NH4+].[Cl-]>CCOC(C)=O>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][N:13]([C:25](=[O:26])[CH2:24][N:20]2[C:21]([CH3:23])=[CH:22][C:18]([CH3:17])=[N:19]2)[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 572875(3,5-Dimethyl-1H-pyrazol-1-yl)acetic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 10932975Methyl 2-(piperazin-1-yl)benzoate

Product 1

HCID 665997292-{4-[2-(3,5-Dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-benzoic acid methyl esterYield 85.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a vial containing the 2-piperazin-1-yl-benzoic acid methyl ester (0.667 g, 3.03 mmol) is added a pre-mixed solution containing (3,5-dimethyl-pyrazol-1-yl)-acetic acid (0.428 g, 2.78 mmol) and carbonyl diimidazole (0.567 g, 3.50 mmol). The mixture is stirred overnight and then diluted with 200 mL of EtOAc followed by 200 mL of sat. NH4Cl. The organic phase is washed with 2×200 mL of H2O and 1×200 mL of brine. The organic phase is dried with MgSO4, filtered and concentrated to give 0.849 g of 2-{4-[2-(3,5-dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-benzoic acid methyl ester.

Workup

  1. additionis added a pre-mixed solution
  2. washThe organic phase is washed with 2×200 mL of H2O and 1×200 mL of brine
  3. dry with materialThe organic phase is dried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-e0d41b05ed414d209f28cc350e1aac4f
Source dataset
uspto-grants-2013_05
Patent number
US08450317B2

Reaction notes

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