Water → HCID 24952549, compound

HRID 1879118Notes

Reaction equation

HRID 1879118 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][C:3]=1[C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]([O:28]CC)=[O:27])=[CH:21][CH:20]=1)=[O:17].O>C(O)(=O)C.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:4][C:3]=1[C:16]([NH:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][C:26]([OH:28])=[O:27])=[CH:23][CH:24]=1)=[O:17]

Participants

5

Reactant 2

HCID 962WaterHCID 59163350HCID 59163350, compound

Product 1

HCID 24952549HCID 24952549, compoundYield 48.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of ethyl {4-[({2-chloro-5-[(phenylmethyl)amino]phenyl}carbonyl)amino]phenyl}acetate (90 mg, 0.21 mmol) in acetic acid (2 ml) and 2M HCl (2 ml) was heated at 90° C. for 2 hours. On cooling water was added then solvent evaporated in vacuo and azeotroped with toluene. The residue was purified by MDAP to afford the title compound as a white solid (40 mg). MS (ES+) m/z 395 [M+H]+ (C22H1935ClN2O3). 1H-NMR (400 MHz, d6-DMSO) δ 3.51 (2H, s), 4.30 (2H, d, J 4.4), 6.63-6.73 (3H, m), 7.15-7.36 (10H, m), 10.3 (1H, s).

Workup

  1. additionwas added
  2. customsolvent evaporated in vacuo
  3. customazeotroped with toluene
  4. customThe residue was purified by MDAP

Sources & evidence

ORD record
ord-46c9b5628e184ef9ad2abdf542c9a060
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Reaction notes

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