Dichloromethane → HCID 23149650, 화합물

HRID 2195636노트

반응식

HRID 2195636 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.[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]1[CH2:36][CH2:35][CH2:34][CH2:33]1>O>[N:32]1([C:23]2[CH:24]=[CH:25][C:26]([C:28]([F:30])([F:31])[F:29])=[CH:27][C:22]=2[NH:21][C:2](=[O:9])[C:3]2[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=2)[CH2:36][CH2:35][CH2:34][CH2:33]1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 5187512-(Pyrrolidin-1-yl)-5-(trifluoromethyl)anilineHCID 12262826Isonicotinoyl chloride hydrochloride

생성물 1

HCID 23149650HCID 23149650, 화합물수율 97.8%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

Isonicotinoyl chloride hydrochloride (705 mg, 3.96 mmol, commercially available product) and triethylamine (823 μl, 5.94 mmol) were sequentially added at 0° C. to a dichloromethane (10 ml) solution of 1-[2-amino-4-(trifluoromethyl)phenyl]pyrrolidine (516 mg, 2.24 mmol), obtained as described in Referential Example 3-2. The resulting mixture was warmed to room temperature and stirred for five 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 (25 g, hexane/ethyl acetate=1/2). Thus, N-[2-(1-pyrrolidinyl)-5-(trifluoromethyl)phenyl]isonicotinamide (GIF-0617) (734 mg, 97.8%) was yielded as a colorless solid.

후처리

  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 (25 g, hexane/ethyl acetate=1/2)

출처 및 근거

ORD 기록
ord-5357833f09e34c10b5694d26ede52251
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338362B2

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