Ethylamine → HCID 86669831, 화합물

HRID 1620270노트

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HRID 1620270 반응식
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:16])=[C:7]([O:14][CH3:15])[CH:8]=2)[N:3]=1.[CH2:17]([NH2:19])[CH3:18]>C1COCC1>[CH2:17]([NH:19][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:16])=[C:7]([O:14][CH3:15])[CH:8]=2)[N:3]=1)[CH3:18]

참가 물질

4

반응물 2

HCID 6341EthylamineHCID 21891887HCID 21891887, 화합물2회

생성물 1

HCID 86669831HCID 86669831, 화합물수율 46%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
150 °C

실험 절차

To a stirred solution of 2-chloro-7-fluoro-6-methoxyquinoline-3-carbaldehyde SMA 44034 (219 mg, 0.91 mmol) in THF (10 mL) in a 20 mL microwave vial equipped with a magnetic stirrer was added ethylamine (2 M in THF, 4.50 mL, 9.00 mmol) and the mixture was stirred at 150° C. for 2 h under microwave irradiation. After cooling to RT, the volatiles were removed under vacuum at 40° C. and the resulting yellow oil was taken up in a 2 N aq. HCl solution (15 mL) and stirred for 15 min at RT then neutralised with a 2 N aq. NaOH solution (15 mL). The mixture was extracted with CH2Cl2:MeOH=9:1 (50 mL) and the organic phase was washed with brine (10 mL), dried over Na2SO4, filtered, and concentrated at 40° C. under vacuum. Purification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 75:25) gave 2-(ethylamino)-7-fluoro-6-methoxyquinoline-3-carbaldehyde CCH 42068 as a yellow oil (105 mg, 46% yield).

후처리

  1. temperatureAfter cooling to RT
  2. customthe volatiles were removed under vacuum at 40° C.
  3. stirringstirred for 15 min at RT
  4. extractionThe mixture was extracted with CH2Cl2
  5. washMeOH=9:1 (50 mL) and the organic phase was washed with brine (10 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated at 40° C. under vacuum
  9. customPurification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 75:25)

출처 및 근거

ORD 기록
ord-3b1f0994461645be98d90656858eac30
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772316B2

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