Ammonia → 5-[2-(Acetylamino)pyridin-4-yl]-2-(2-chlorophenyl)-3-furamide

HRID 537036Notes

Reaction equation

HRID 537036 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:15][C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])=[C:13]([C:23]([OH:25])=O)[CH:12]=2)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2].N.C[N:28](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CC(N(C)C)=O>C(Cl)Cl.O>[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:15][C:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])=[C:13]([C:23]([NH2:28])=[O:25])[CH:12]=2)[CH:8]=[CH:7][N:6]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 31374DimethylacetamideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 667483155-[2-(Acetylamino)pyridin-4-yl]-2-(2-chlorophenyl)-3-furoic acid

Product 1

HCID 568393735-[2-(Acetylamino)pyridin-4-yl]-2-(2-chlorophenyl)-3-furamideYield 62.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-[2-(acetylamino)pyridin-4-yl]-2-(2-chlorophenyl)-3-furoic acid (0.10 g, 0.28 mmol) in DCM (15 mL) was added ammonia (0.5 M in 1,4-dioxane, 4.5 mL), TBTU (0.18 g, 0.56 mmol) and DMA (0.49 mL, 2.8 mmol). The mixture was allowed to stir at rt overnight. The reaction mixture was diluted with water and extracted with DCM. The organic solutions were combined, washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 5-[2-(acetylamino)pyridin-4-yl]-2-(2-chlorophenyl)-3-furamide (0.062 g, 62%) as a white solid. LCMS (FA): m/z=356.5 (M+H).

Workup

  1. extractionextracted with DCM
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4a6186c298a94036973e99807771297a
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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