Pyridine → HCID 2676472, compound

HRID 642083Notes

Reaction equation

HRID 642083 reaction equation
N[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[C:12]([C:14]1[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][CH:15]=1)#[N:13].[N:23]1C=CC=CC=1>>[C:12]([C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH:23][C:3]2[CH:4]=[C:5]([CH:10]=[CH:11][CH:2]=2)[C:6]([O:8][CH3:9])=[O:7])=[O:19])=[CH:16][CH:15]=1)#[N:13]

Participants

4

Reactant 3

HCID 1049PyridineHCID 12082Methyl 4-aminobenzoateHCID 801724-Cyanobenzoyl chloride

Product 1

HCID 2676472HCID 2676472, compound

Procedure

To a solution of methyl 4-aminobenzoate (500 mg, 3.31 mmol) in anydrous pyridine (10 mL) was added dropwise 4-cyanobenzoyl chloride (660 mg, 4.0 mmol) at 0° C. After 5 min the temperature was allowed to warm up to rt. After 3 hrs aminomethyl resin (Polymers Laboratories PL-AMS, 1.96 mmol/g, 720 mg) was added and the resulting mixture was stirred overnight at rt. After rinsing the resin and filtration, water (25 mL) was added to the filtrate and a beige solid precipated out. Filtration and washing with water gave a solid which was dried under vacuo at 60° C. for 5 hrs. The title compound (774 mg) was obtained as a beige solid (83%) in 97.7% purity by HPLC (MaxPlot detection between 230 and 400 nm) 1H NMR (300 MHz, DMSO-d6) δ 10.68 (s, 1H), 8.45 (m, 1H), 8.12 (d, J=8.3 Hz, 2H), 8.05 (m, 3H), 7.71 (d, J=7.8 Hz, 1H), 7.52 (dd, J=7.9, 7.8 Hz, 1H), 3.86 (s, 3H).

Workup

  1. additionAfter 3 hrs aminomethyl resin (Polymers Laboratories PL-AMS, 1.96 mmol/g, 720 mg) was added
  2. washAfter rinsing
  3. filtrationthe resin and filtration, water (25 mL)
  4. additionwas added to the filtrate
  5. filtrationFiltration
  6. washwashing with water
  7. customgave a solid which
  8. customwas dried under vacuo at 60° C. for 5 hrs

Sources & evidence

ORD record
ord-1dc49c009e034217a1fc5e86c22f4317
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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