HCID 59608430, compound → HCID 25256357, compound

HRID 2067162Notes

Reaction equation

HRID 2067162 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])=[CH:4][C:3]=1[C:17]([NH:19][CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27]C)=[O:26])=[CH:23][CH:22]=1)=[O:18]>C(O)(=O)C.Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])=[CH:4][C:3]=1[C:17]([NH:19][CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:29][CH:30]=1)=[O:18]

Participants

4

Reactant 1

HCID 59608430HCID 59608430, compound

Product 1

HCID 25256357HCID 25256357, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A solution of methyl 4-({[(2-chloro-5-{[(2-chlorophenyl)methyl]oxy}phenyl)carbonyl]amino}methyl)benzoate (113 mg, 0.25 mmol) in acetic acid (10 ml) and 2M HCl (10 ml) was heated at 90° C. for 6 hours. Heating continued at 90° C. overnight. A solid crashed out on cooling. The resulting solid was filtered, washed with water and dried to give the title compound as a white solid (67 mg). MS (ES+) m/z 430 [M+H]+ (C22H1735Cl2NO4). 1H-NMR (400 MHz, d6-DMSO) δ 4.51 (2H,d, J 6.0), 5.20 (2H,s), 7.11-7.16 (2H,m), 7.37-7.54 (6H,m), 7.59-7.62 (1H,m), 7.91-7.94 (2H,m), 9.10 (1H,t, J 6.0), 12.89 (1H, s).

Workup

  1. temperatureHeating
  2. temperatureon cooling
  3. filtrationThe resulting solid was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-da2701bec85b4c098b1c784410182a02
Source dataset
uspto-grants-2012_10
Patent number
US08293798B2

Reaction notes

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