HCID 22038481, compound → HCID 22038521, compound

HRID 1790043Notes

Reaction equation

HRID 1790043 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])[C:15]3[CH2:14][CH2:13][N:12](CC4C=CC(OC)=CC=4OC)[C:11](=[O:36])[C:10]=3[C:9]=2[CH3:37])=[CH:4][CH:3]=1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])[C:15]3[CH2:14][CH2:13][NH:12][C:11](=[O:36])[C:10]=3[C:9]=2[CH3:37])=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 22038481HCID 22038481, compound

Product 1

HCID 22038521HCID 22038521, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-5-(2,4-dimethoxybenzyl)-3-methyl-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (1.13 g, 2.03 mmol, Table 2, entry 176) in trifluoroacetic acid (40 mL) was heated at reflux temperature for 2 h. Trifluoroacetic acid was removed by evaporation under reduced pressure, and the residue was purified by silica gel chromatography. Elution first with 50% ethyl acetate in hexane followed by ethyl acetate gave a yellow solid (600 mg, 73%). LC-MS m/z (MH+) 405.0, retention time 3.84 min (method 2).

Workup

  1. temperatureat reflux temperature for 2 h
  2. customTrifluoroacetic acid was removed by evaporation under reduced pressure
  3. customthe residue was purified by silica gel chromatography
  4. washElution first with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-2ffbd025e5a443f88cec01ba25c5378e
Source dataset
uspto-grants-2006_07
Patent number
US07071207B2

Reaction notes

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