Triethylamine → 3,5-difluoro-N-(4-methyl-1,2,5-oxadiazol-3-yl)isonicotinamide

HRID 575887Notes

Reaction equation

HRID 575887 reaction equation
[F:1][C:2]1[CH:10]=[N:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=O.[CH3:12][C:13]1[C:14]([NH2:18])=[N:15][O:16][N:17]=1.C(N(CC)CC)C.C(P1(=O)OP(=O)(CCC)OP(=O)(CCC)O1)CC>ClCCl.CN(C1C=CN=CC=1)C>[F:11][C:7]1[CH:8]=[N:9][CH:10]=[C:2]([F:1])[C:3]=1[C:4]([NH:18][C:14]1[C:13]([CH3:12])=[N:17][O:16][N:15]=1)=[O:6]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 286743-Amino-4-methylfurazanHCID 111923Propylphosphonic anhydrideHCID 201118793,5-Difluoroisonicotinic acid

Product 1

HCID 682907883,5-difluoro-N-(4-methyl-1,2,5-oxadiazol-3-yl)isonicotinamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

200 mg (1.26 mmol) of 3,5-difluoroisonicotinic acid and 125 mg (1.26 mmol) of 4-methyl-1,2,5-oxadiazol-3-amine are dissolved at RT in 6 ml of dichloromethane, and 0.88 ml (6.29 mmol) of triethylamine, 31 mg (0.25 mmol) of DMAP and 1.20 g (1.89 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 5 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: 100 mg (31%).

Workup

  1. washwashed twice with 5 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-2396fe2f89d441e0bf309779eb2ca148
Source dataset
uspto-grants-2015_05
Patent number
US09035064B2

Reaction notes

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