Triethylamine → HCID 67215265, compound

HRID 1677561Notes

Reaction equation

HRID 1677561 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[N+:12]([O-:14])=[O:13])[C:6](Cl)=[O:7].C(N(CC)CC)C.[CH:22]1[N:23]=[CH:24][N:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=12>ClCCCl>[CH:22]1[N:23]=[C:24]([C:6]([C:5]2[CH:9]=[CH:10][C:11]([N+:12]([O-:14])=[O:13])=[C:3]([O:2][CH3:1])[CH:4]=2)=[O:7])[N:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 274090Imidazo(1,5-a)pyridineHCID 111276553-methoxy-4-nitro-benzoyl Chloride

Product 1

HCID 67215265HCID 67215265, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

11.5 g (0.053 mol) of 3-methoxy-4-nitrobenzoyl chloride and 7.8 ml (0.056 mol) of triethylamine are added to 3 g (0.025 mol) of imidazo[1,5-a]pyridine [described in J. Chem. Soc., (1955), 2834-2836] dissolved in 100 ml of 1,2-dichloroethane. The mixture is stirred at ambient temperature for 2 hours. The reaction medium is concentrated under reduced pressure and the residue is then taken up in dichloromethane and a saturated aqueous sodium bicarbonate solution. The organic phase is separated by settling, washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated under reduced pressure. The residue is taken up in dichloromethane and purified by filtration through a bed of silica gel. After evaporation, 7.1 g of a yellow solid are collected. Melting point: 183° C.; 1H NMR (d6-DMSO): 4.01 (3H, s), 7.35-7.40 (1H, m), 7.47-7.54 (1H, m), 7.97 (1H, s), 8.06-8.11 (3H, m), 8.15 (1H, s), 9.77 (1H, d).

Workup

  1. concentrationThe reaction medium is concentrated under reduced pressure
  2. customThe organic phase is separated
  3. washwashed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. filtrationpurified by filtration through a bed of silica gel
  7. customAfter evaporation, 7.1 g of a yellow solid
  8. customare collected

Sources & evidence

ORD record
ord-470d0670d67441a6a55f787c95fb6959
Source dataset
uspto-grants-2011_08
Patent number
US08008321B2

Reaction notes

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