Pyridine → HCID 1548488, compound

HRID 642068Notes

Reaction equation

HRID 642068 reaction equation
[NH2:1][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].N1C=CC=C[CH:24]=1>>[C:12]([C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:24])=[O:7])=[CH:10][CH:11]=2)=[O:19])=[CH:16][CH:15]=1)#[N:13]

Participants

4

Reactant 3

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

Product 1

HCID 1548488HCID 1548488, compound

Procedure

To a solution of methyl 4-aminobenzoate (500 mg, 3.31 mmol) in anhydrous pyridine (10 mL) was added dropwise 4-cyanobenzoyl chloride (660 mg) at 0° C. After 5 min the temperature was allowed to warm up to rt. After 90 min aminomethyl resin (Polymers Laboratories PL-AMS, 1.93 mmol/g, 720 mg) was added and the resulting mixture was stirred overnight at rt. After filtration and rinsing the resin, water (125 mL) was added to the filtrate and a white solid precipated out. Filtration and washing with water gave a solid which was dried under vacuo at 60° C. overnight. The title compound (854 mg) was obtained as a pale yellow solid (92%) in 95.2% purity by HPLC (MaxPlot detection between 230 and 400 nm).

Workup

  1. additionAfter 90 min aminomethyl resin (Polymers Laboratories PL-AMS, 1.93 mmol/g, 720 mg) was added
  2. filtrationAfter filtration
  3. washrinsing the resin, water (125 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. overnight

Sources & evidence

ORD record
ord-8de42b770b7c49ff8d563eddd19fb90b
Source dataset
uspto-grants-2010_04
Patent number
US07696231B2

Reaction notes

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