Pyridine → HCID 58288486, compound

HRID 1969050Notes

Reaction equation

HRID 1969050 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[CH2:23][NH2:24])[CH:7]=1)[CH3:2].N1C=CC=CC=1.[Cl:32][C:33]1[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=1>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][C:14]=2[CH2:23][NH:24][C:37](=[O:38])[C:36]2[CH:40]=[CH:41][C:33]([Cl:32])=[CH:34][CH:35]=2)[CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 85014-Chlorobenzoyl chlorideHCID 58288488HCID 58288488, compound

Product 1

HCID 58288486HCID 58288486, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To [3-(2-aminomethyl-4-trifluoromethyl-phenoxy)-phenyl]-acetic acid ethyl ester (0.084 g, 0.24 mmol) and pyridine (2.0 mL) in CH2Cl2 (2.5 mL) was added 4-chlorobenzoyl chloride (0.04 mL, 0.29 mmol), and the reaction was stirred for 30 minutes at room temperature. The mixture was partitioned between CH2Cl2 and 1N aqueous HCl, and the organic layer was separated and washed twice with 1N aqueous HCl. The organic layer was dried and concentrated, resulting in the formation of a white precipitate. The precipitate was filtered off, and the filtrate was concentrated to give the title compound.

Workup

  1. customThe mixture was partitioned between CH2Cl2 and 1N aqueous HCl
  2. customthe organic layer was separated
  3. washwashed twice with 1N aqueous HCl
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customresulting in the formation of a white precipitate
  7. filtrationThe precipitate was filtered off
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-dee14350804c436ba5aa62fc4bf520fb
Source dataset
uspto-grants-2013_04
Patent number
US08426449B2

Reaction notes

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