Triethylamine → 5-chloro-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(trifluoromethyl)pyridine-2-carboxamide

HRID 575888Notes

Reaction equation

HRID 575888 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([F:14])([F:13])[F:12])[C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.[CH3:15][C:16]1[C:17]([NH2:21])=[N:18][O:19][N:20]=1.C(N(CC)CC)C.C(P1(=O)OP(=O)(CCC)OP(=O)(CCC)O1)CC>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([F:14])([F:13])[F:12])[C:5]([C:8]([NH:21][C:17]2[C:16]([CH3:15])=[N:20][O:19][N:18]=2)=[O:10])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 286743-Amino-4-methylfurazanHCID 111923Propylphosphonic anhydrideHCID 455880585-Chloro-3-(trifluoromethyl)pyridine-2-carboxylic acid

Product 1

HCID 682908695-chloro-N-(4-methyl-1,2,5-oxadiazol-3-yl)-3-(trifluoromethyl)pyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

300 mg (1.33 mmol) of 5-chloro-3-(trifluoromethyl)pyridine-2-carboxylic acid and 132 mg (1.33 mmol) of 4-methyl-1,2,5-oxadiazol-3-amine are dissolved at RT in 10 ml of CH2Cl2, and 0.19 ml (1.33 mmol) of triethylamine, 32 mg (0.27 mmol) of DMAP and 1.27 g (2.00 mmol) of 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane 2,4,6-trioxide (50% solution in THF) are added. The reaction mixture is stirred at RT for 20 h and then washed twice with 10 ml each time of water. The organic phase is dried over Na2SO4 and concentrated. The residue is purified by column chromatography (silica gel, heptane/ethyl acetate). Yield: 250 mg (61%).

Workup

  1. washwashed twice with 10 ml each time of water
  2. dry with materialThe organic phase is dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue is purified by column chromatography (silica gel, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-f82bc14471e8427ebc0efda081c032bd
Source dataset
uspto-grants-2015_05
Patent number
US09035064B2

Reaction notes

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