Triethylamine → 2-chloro-N-(1,2,5-oxadiazol-3-yl)-6-(trifluoromethyl)nicotinamide

HRID 575885Notes

Reaction equation

HRID 575885 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N(CC)CC)C.C[C:23]1[C:24]([NH2:28])=[N:25][O:26][N:27]=1>ClCCl>[Cl:1][C:2]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([NH:28][C:24]1[CH:23]=[N:27][O:26][N:25]=1)=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 286743-Amino-4-methylfurazanHCID 27782102-Chloro-6-(trifluoromethyl)nicotinic acid

Product 1

HCID 889241062-chloro-N-(1,2,5-oxadiazol-3-yl)-6-(trifluoromethyl)nicotinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

239 mg (1.06 mmol) of 2-chloro-6-(trifluoromethyl)nicotinic acid and 1.6 g (2.0 mmol) of Mukaiyama reagent on polymer (1.25 mmol/g) are admixed with 15 ml of dichloromethane (abs.) and 0.31 g (3.03 mmol) of triethylamine. Then 100 mg (1.01 mmol) of 4-methyl-1,2,5-oxadiazol-3-ylamine are added. The reaction mixture is stirred at room temperature (RT) for 14 h. Subsequently, the solid is removed by means of a frit and washed with 10 ml of dichloromethane. The filtrate is concentrated and purified by chromatography using a silica gel column with heptane/ethyl acetate. Yield: 52 mg (16%).

Workup

  1. customSubsequently, the solid is removed by means of a frit
  2. washwashed with 10 ml of dichloromethane
  3. concentrationThe filtrate is concentrated
  4. custompurified by chromatography

Sources & evidence

ORD record
ord-0a021f99ac64470b893a029af2dc370c
Source dataset
uspto-grants-2015_05
Patent number
US09035064B2

Reaction notes

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