Benzoyl chloride → N-(2-{4-[2-(3,5-dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-phenyl)-benzamide

HRID 1810965Notes

Reaction equation

HRID 1810965 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:23])[CH2:15][N:16]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[N:17]2)[CH2:10][CH2:9]1.C(N(C(C)C)CC)(C)C.[C:33](Cl)(=[O:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>C(Cl)Cl>[CH3:22][C:18]1[CH:19]=[C:20]([CH3:21])[N:16]([CH2:15][C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[NH:1][C:33](=[O:40])[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH2:9][CH2:10]2)=[O:23])[N:17]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 81531DiisopropylethylamineHCID 595487551-[4-(2-Amino-phenyl)-piperazin-1-yl]-2-(3,5-dimethyl-pyrazol-1-yl)-ethanone

Product 1

HCID 59548829N-(2-{4-[2-(3,5-dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-phenyl)-benzamideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 1-[4-(2-amino-phenyl)-piperazin-1-yl]-2-(3,5-dimethyl-pyrazol-1-yl)-ethanone (0.042 g, 0.136 mmol) is dissolved in 1.5 mL of CH2Cl2. To this is added diisopropylethyl amine (0.046 mL, 0.250 mmol) and benzoyl chloride (0.018 mL, 0.150). The mixture is stirred for 60 h. The reaction is quenched with 2 mL of saturated NH4Cl and extracted in the reaction vial with 2×2 mL of CH2Cl2. The organic phase is concentrated. The residue is purified using a SiO2 prep plate eluting with (75% EtOAc/hexanes) to give 58.1 mg of N-(2-{4-[2-(3,5-dimethyl-pyrazol-1-yl)-acetyl]-piperazin-1-yl}-phenyl)-benzamide in 100% Yield. MS: MH+=418.2.

Workup

  1. customThe reaction is quenched with 2 mL of saturated NH4Cl
  2. extractionextracted in the reaction vial with 2×2 mL of CH2Cl2
  3. concentrationThe organic phase is concentrated
  4. customThe residue is purified
  5. washeluting with (75% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4bd187fd88ba4b709ab8774289306a0b
Source dataset
uspto-grants-2013_01
Patent number
US08362249B2

Reaction notes

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