Dichloromethane → N-[5-chloro-2-(1-piperidinyl)phenyl]isonicotinamide

HRID 2099096

반응식

HRID 2099096 반응식
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.[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)=[C:26]([CH:28]=1)[NH2:27]>CN(C)C1C=CN=CC=1.O>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([N:29]2[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]2)=[C:26]([NH:27][C:2](=[O:9])[C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)[CH:28]=1

참가 물질

7

반응물 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 2853175-Chloro-2-(piperidin-1-yl)anilineHCID 12262826Isonicotinoyl chloride hydrochloride

생성물 1

HCID 23149647N-[5-chloro-2-(1-piperidinyl)phenyl]isonicotinamide수율 31.8%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매

실험 절차

Isonicotinoyl chloride hydrochloride (350 mg, 1.96 mmol, commercially available product), triethylamine (740 μl, 5.30 mmol), and a catalytic amount of 4-(dimethylamino)pyridine were sequentially added at room temperature to a dichloromethane (10 ml) solution of 5-chloro-2-(1-piperidinyl)aniline (378 mg, 1.79 mmol), obtained as described in Referential Example 15-2. The resulting mixture was stirred for 19 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 (200 g, hexane/ethyl acetate=1/1). Thus, N-[5-chloro-2-(1-piperidinyl)phenyl]isonicotinamide (GIF-0341) (180 mg, 31.8%) was yielded as a colorless solid.

후처리

  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 (200 g, hexane/ethyl acetate=1/1)

출처 및 근거

ORD 기록
ord-84a1fc2d66cd4711b25ad11921a7ecc4
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569536B2

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