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

HRID 718047Notes

Reaction equation

HRID 718047 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-f7051a804df6433a935f704e9a6ea253
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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