Dimethylamine → HCID 67048044, 화합물

HRID 606912노트

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HRID 606912 반응식
Cl[CH2:2][C:3]1[CH:4]=[C:5]([C:10]#[C:11][C:12]2[CH:13]=[N:14][CH:15]=[C:16]([CH:19]=2)[C:17]#[N:18])[CH:6]=[CH:7][C:8]=1[F:9].[CH3:20][NH:21][CH3:22]>O1CCCC1.C(OCC)(=O)C.C(OCC)C>[CH3:20][N:21]([CH2:2][C:3]1[CH:4]=[C:5]([C:10]#[C:11][C:12]2[CH:13]=[N:14][CH:15]=[C:16]([CH:19]=2)[C:17]#[N:18])[CH:6]=[CH:7][C:8]=1[F:9])[CH3:22]

참가 물질

6

반응물 2

HCID 674DimethylamineHCID 67047920HCID 67047920, 화합물

생성물 1

HCID 67048044HCID 67048044, 화합물수율 58%

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
70 °C

실험 절차

Treat 5-(3-chloromethyl-4-fluorophenylethynyl)-nicotinonitrile, (prepared as described in PREPARATION 32), (100 mg, 0.37 mmol) with a 2.0 M solution of dimethylamine in tetrahydrofuran (3 mL) and heat at 70° C. in a sealed tube for 2 h. Cool to room temperature, dilute with ethyl acetate, and wash with an aqueous saturated solution of sodium bicarbonate and an aqueous saturated solution of sodium chloride. Dry (sodium sulfate), filter, and concentrate. Purify by silica gel chromatography, eluting with a gradient from 50:50 hexanes:dichloromethane to 90:10 (50:50 hexanes:dichloromethane):methanol, to give a yellow oil. Dissolve the oil in diethyl ether and extract twice with 1 N hydrochloric acid. Combine the aqueous layers and make basic with a 1 N sodium hydroxide. Extract the resultant purple aqueous layer three times with ethyl acetate. Combine the organic extracts, wash with an aqueous saturated solution of sodium chloride, dry (sodium sulfate), filter, and concentrate to an oil. Concentration of the oil from diethyl ether provides the title compound as a crystalline solid (60 mg, 58%).

후처리

  1. temperatureCool to room temperature
  2. washwash with an aqueous saturated solution of sodium bicarbonate
  3. dry with materialDry (sodium sulfate)
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify by silica gel chromatography
  7. washeluting with a gradient from 50:50 hexanes
  8. customdichloromethane to 90:10 (50:50 hexanes:dichloromethane):methanol, to give a yellow oil
  9. extractionextract twice with 1 N hydrochloric acid
  10. extractionExtract the resultant purple aqueous layer three times with ethyl acetate
  11. washwash with an aqueous saturated solution of sodium chloride
  12. dry with materialdry (sodium sulfate)
  13. filtrationfilter
  14. concentrationconcentrate to an oil

출처 및 근거

ORD 기록
ord-09f80bb53f2c4c56aa00f9521ee7b09e
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915424B2

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