4-Aminopyridine → 2,4,6-trichloro-N-(pyridin-4-yl)benzamide

HRID 449861Notes

Reaction equation

HRID 449861 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[C:7]([Cl:12])[C:3]=1[C:4]([OH:6])=O.[NH2:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:12][C:7]1[CH:8]=[C:9]([Cl:11])[CH:10]=[C:2]([Cl:1])[C:3]=1[C:4]([NH:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=1)=[O:6]

Participants

6

Reactant 4

HCID 17274-AminopyridineHCID 57642,4,6-Trichlorobenzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 596185842,4,6-trichloro-N-(pyridin-4-yl)benzamideYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,4,6-trichlorobenzoic acid (224 mg, 10 mmol), 4-aminopyridine (141 mg, 1.5 mmol), HATU (1140 mg, 3 mmol), and DIPEA (646 mg, 5 mmol) in 5 mL anhydrous DMF was stirred under nitrogen at room temperature overnight. The reaction mixture was poured into ice-water (20 mL) and extracted EtOAc (2×50 mL). The combined organics were evaporated to dryness in vacuum and the residue was purified by silica gel column chromatography (EtOAc) to afford the desired product (72 mg, yield: 24%). 1HNMR: (CD3OD-d4, 400 MHz): δ 8.38 (d, J=6.0 Hz, 2H), 7.65 (d, J=6.0 Hz, 2H), 7.52 (s, 2H). LCMS (ESI) m/z: 301.1 [M+H+].

Workup

  1. extractionextracted EtOAc (2×50 mL)
  2. customThe combined organics were evaporated to dryness in vacuum
  3. customthe residue was purified by silica gel column chromatography (EtOAc)

Sources & evidence

ORD record
ord-698f4ecabd8a40ad9c081964378bcdd0
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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