Triethylamine → 2-(benzyloxy)-N-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)benzamide

HRID 1946580Notes

Reaction equation

HRID 1946580 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[Cl:24][C:25]1[C:30]([NH2:31])=[CH:29][CH:28]=[C:27]([C:32]([F:35])([F:34])[F:33])[N:26]=1.C(N(CC)CC)C>C1COCC1.CN(C=O)C.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH:31][C:30]1[C:25]([Cl:24])=[N:26][C:27]([C:32]([F:34])([F:33])[F:35])=[CH:28][CH:29]=1)=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18105812-Benzyloxybenzoic acidHCID 27376462-Chloro-6-(trifluoromethyl)pyridin-3-amine

Product 1

HCID 597836062-(benzyloxy)-N-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)benzamideYield 73%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 2-(benzyloxy)benzoic acid (2.55 g, 11.19 mmol) and oxalyl chloride (2.84 g, 22.39 mmol) in THF (20 mL) was added a few drops of DMF (0.012 mL, 0.153 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and further stirred 30 minutes, diluted with toluene and then solvent evaporated. The residue was taken up in THF (20 mL) and to this solution was added 2-chloro-6-(trifluoromethyl)pyridin-3-amine (2.0 g, 10.18 mmol) at 0° C. followed by the addition of triethylamine (4.68 mL, 33.6 mmol). The reaction mixture was allowed to stir 3 days at room temperature then quenched with saturated bicarbonate solution, extracted with EtOAc and solvent evaporated to afford title compound 72 (3.0 g, 73% yield) after purification by flash chromatography (0 to 100% ethyl acetate in hexane). LRMS (ESI): (calc) 406.07 (found) 407.4 (MH)+.

Workup

  1. customsolvent evaporated
  2. customthen quenched with saturated bicarbonate solution
  3. extractionextracted with EtOAc and solvent
  4. customevaporated

Sources & evidence

ORD record
ord-6445b47fa3ca4492a02727469ffcd765
Source dataset
uspto-grants-2013_03
Patent number
US08399452B2

Reaction notes

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