Dichloromethane → HCID 57793949, compound

HRID 2410275Notes

Reaction equation

HRID 2410275 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.[CH3:21][C@H:22]1[CH2:27][CH2:26][CH2:25][CH2:24][N:23]1[C:28]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][C:29]=1[NH2:30]>O>[CH3:21][C@H:22]1[CH2:27][CH2:26][CH2:25][CH2:24][N:23]1[C:28]1[CH:34]=[CH:33][C:32]([C:35]([F:37])([F:36])[F:38])=[CH:31][C:29]=1[NH:30][C:2](=[O:9])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 12262826Isonicotinoyl chloride hydrochlorideHCID 40788210HCID 40788210, compound

Product 1

HCID 57793949HCID 57793949, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Isonicotinoyl chloride hydrochloride (466 mg, 2.61 mmol, commercially available product) and triethylamine (600 μl, 4.30 mmol) were sequentially added at 0° C. to a dichloromethane (5 ml) solution of (S)-2-(2-methyl-1-piperidinyl)-5-(trifluoromethyl)aniline (223 mg, 0.863 mmol), obtained as described in [Referential Example 2-2]. The resulting mixture was warmed to room temperature and stirred for 19.5 hours. Water was added to the mixture, and the resulting mixture was extracted three times with ethyl acetate. 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 (25 g, hexane/ethyl acetate=1.5/1). Thus, (S)—N-[2-(2-methyl-1-piperidinyl)-5-(trifluoromethyl)phenyl]isonicotinamide (GIF-0613) (293 mg, 93.4%) was yielded as an colorless oily material.

Workup

  1. customobtained
  2. extractionthe resulting mixture was extracted three times with ethyl acetate
  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 (25 g, hexane/ethyl acetate=1.5/1)

Sources & evidence

ORD record
ord-9c535660b529465c9088fa5bb4e52d6f
Source dataset
uspto-grants-2014_08
Patent number
US08816089B2

Reaction notes

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