Phthalic Anhydride → HCID 57855653, compound

HRID 1178125Notes

Reaction equation

HRID 1178125 reaction equation
[O:1]=[C:2]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)[CH2:3][NH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)=[O:6].[C:25]1(=[O:35])[O:30][C:28](=[O:29])[C:27]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:26]12>C1(C)C=CC=CC=1>[C:10]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=[CH:8][C:7]([C:5]([NH:4][CH2:3][C:2]([N:19]2[CH2:24][CH2:23][N:22]([C:25]([C:26]3[CH:34]=[CH:33][CH:32]=[CH:31][C:27]=3[C:28]([OH:30])=[O:29])=[O:35])[CH2:21][CH2:20]2)=[O:1])=[O:6])=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 57855677Biphenyl-4-carboxylicacid (2-oxo-2-piperazin-1-yl-ethyl)-amide

Product 1

HCID 57855653HCID 57855653, compoundYield 48.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Biphenyl-4-carboxylic acid (2-oxo-2-piperazin-1-yl-ethyl)-amide (150 mg, 0.46 mmol) and phthalic anhydride (69 mg, 0.46 mmol) in toluene (20 mL) were heated to reflux for 2 hours. The reaction mixture was then concentrated under reduced pressure. The resulting residue was purified by Preparative TLC (using silicagel 60F254 coated glass plate (20×20 cm, 1 mm (thickness) as the stationary phase with the mobile phase being 10% MeOH in Chloroform) to afford 106 mg (48.5% yield) of 2-(4-{2-[(biphenyl-4-carbonyl)-amino]-acetyl}-piperazine-1-carbonyl)-benzoic acid, LC-MS purity: 86.97%, 1H NMR: (DMSO) δ 8.6 (t, 1H), 7.9 (d, 2H), 7.85-7.7 (m, 4H), 7.5 (t, 2H), 7.4 (t, 1H), 7.3-7.2 (bs, 2H), 7.0 (bs, 1H), 4.25-4.05 (m, 2H), 3.75-3.4 (m, 6H), 3.1-3.0 (bs, 2H).

Workup

  1. temperatureto reflux for 2 hours
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customThe resulting residue was purified by Preparative TLC (

Sources & evidence

ORD record
ord-9bbf23207b154825abe396b065ece935
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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