Dichloromethane → HCID 23149648, compound

HRID 2410286Notes

Reaction equation

HRID 2410286 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.ClCCl.[NH2:21][C:22]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:23]=1[N:32]([CH2:35][CH3:36])[CH2:33][CH3:34]>O>[CH2:35]([N:32]([CH2:33][CH3:34])[C:23]1[CH:24]=[CH:25][C:26]([C:28]([F:30])([F:29])[F:31])=[CH:27][C:22]=1[NH:21][C:2](=[O:9])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)[CH3:36]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 49621711-N,1-N-diethyl-4-(trifluoromethyl)benzene-1,2-diamineHCID 12262826Isonicotinoyl chloride hydrochloride

Product 1

HCID 23149648HCID 23149648, compoundYield 34.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Isonicotinoyl chloride hydrochloride (88.2 mg, 0.495 mmol, commercially available product) and triethylamine (140 μL, 1.00 mmol) were sequentially added at 0° C. to a dichloromethane (3 ml) solution of 2-amino-1-diethylamino-4-(trifluoromethyl)benzene (103 mg, 0.443 mmol), obtained as described in Referential Example 6-2. The resulting mixture was warmed to room temperature and stirred for one and a half hours. Water was added to the mixture, and the resulting mixture was extracted three times with dichloromethane. The obtained organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (30 g, hexane/ethyl acetate=2/1). Thus, N-[2-diethylamino-5-(trifluoromethyl)phenyl]isonicotinamide (GIF-0347) (51.0 mg, 34.1%) was yielded as a colorless solid.

Workup

  1. customobtained
  2. extractionthe resulting mixture was extracted three times with dichloromethane
  3. washThe obtained organic layer was washed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (30 g, hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-b8b8d5ba5dcf4ee5bf7408df80abbec9
Source dataset
uspto-grants-2014_08
Patent number
US08816089B2

Reaction notes

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