Acetic Anhydride → HCID 22285550, compound

HRID 1062455Notes

Reaction equation

HRID 1062455 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([NH:16][N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[O:15])[N:10]=[C:9]2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])=[CH:4][CH:3]=1.[C:30](OC(=O)C)(=[O:32])[CH3:31]>ClCCl>[C:30]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]([CH3:13])=[C:11]([C:14]([NH:16][N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)=[O:15])[N:10]=[C:9]2[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])=[CH:6][CH:7]=1)(=[O:32])[CH3:31]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 22285397HCID 22285397, compound

Product 1

HCID 22285550HCID 22285550, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(4-Aminophenyl)-2-(2-chlorophenyl)-5-methyl-N-(1-piperidinyl)-1H-imidazole-4-carboxamide (Example 45) (51 mg, 0.12 mmol) was dissolved in dry dichloromethane (2 mL) and treated with acetic anhydride (14 μL, 0.15 mmol) dropwise. The solution was stirred at rt for 4 h, and then the solvent was evaporated to give an amber oil. It was purified by HPLC (YMC-packed Pro C18 15×200 mm column, 30-90% CH3CN in H2O/TFA, 20 mL/min.) to afford an off-white solid (13 mg, 15%): LC-MS m/z 452.3 (MH+), retention time 2.31 min (method 1).

Workup

  1. customthe solvent was evaporated
  2. customto give an amber oil
  3. customIt was purified by HPLC (YMC-packed Pro C18 15×200 mm column, 30-90% CH3CN in H2O/TFA, 20 mL/min.)

Sources & evidence

ORD record
ord-191de32909104df8960acccbac24a508
Source dataset
uspto-grants-2005_11
Patent number
US06960601B2

Reaction notes

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