Pyridine → HCID 67546297, compound

HRID 452963Notes

Reaction equation

HRID 452963 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[CH2:6][N:7]1[C:11]([NH2:12])=[C:10]2[CH2:13][CH2:14][CH2:15][C:9]2=[N:8]1.N1C=CC=CC=1.[CH3:22][O:23][C:24]1[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][C:25]=1[C:26](Cl)=[O:27]>C(Cl)Cl>[CH3:22][O:23][C:24]1[CH:32]=[CH:31][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:29][C:25]=1[C:26]([NH:12][C:11]1[N:7]([CH2:6][C@H:2]2[CH2:3][CH2:4][CH2:5][O:1]2)[N:8]=[C:9]2[CH2:15][CH2:14][CH2:13][C:10]=12)=[O:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 15571508HCID 15571508, compoundHCID 67546041HCID 67546041, compound

Product 1

HCID 67546297HCID 67546297, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Example 32A (340 mg, 1.64 mmol) and pyridine (535 μL, 6.56 mmol) in CH2Cl2 (20 mL) was added 2-methoxy-5-(trifluoromethyl)benzoyl chloride (470 mg, 1.97 mmol) dropwise. The mixture was stirred at ambient temperature for 1 h. The mixture was concentrated under reduced pressure and was purified by column chromatography (SiO2, 40% hexanes/EtOAc) to provide the title compound 550 mg (82%). MS (DCI/NH3) m/z 410 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customwas purified by column chromatography (SiO2, 40% hexanes/EtOAc)

Sources & evidence

ORD record
ord-6b40bc13280846af968be15c775af0c6
Source dataset
uspto-grants-2013_07
Patent number
US08492371B2

Reaction notes

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