N-(2-aminoethyl)acetamide → N-(2-(6-(Cyclopropylmethoxy)-3-formylquinolin-2-ylamino)ethyl)acetamide

HRID 1620305노트

반응식

HRID 1620305 반응식
Cl[C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14][CH2:15][CH:16]3[CH2:18][CH2:17]3)[CH:8]=2)[N:3]=1.[NH2:19][CH2:20][CH2:21][NH:22][C:23](=[O:25])[CH3:24]>C1COCC1>[CH:16]1([CH2:15][O:14][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[N:3]=[C:2]([NH:19][CH2:20][CH2:21][NH:22][C:23](=[O:25])[CH3:24])[C:11]([CH:12]=[O:13])=[CH:10]3)[CH2:18][CH2:17]1

참가 물질

4

반응물 2

HCID 66082N-(2-aminoethyl)acetamideHCID 866698362-Chloro-6-(cyclopropylmethoxy)quinoline-3-carbaldehyde2회

생성물 1

HCID 86669837N-(2-(6-(Cyclopropylmethoxy)-3-formylquinolin-2-ylamino)ethyl)acetamide수율 38%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
160 °C

실험 절차

To a stirred solution of 2-chloro-6-(cyclopropylmethoxy)quinoline-3-carbaldehyde SLA 47086 (770 mg, 2.94 mmol) in THF (15 mL) in a 20 mL microwave vial equipped with a magnetic stirrer was added N-(2-aminoethyl)acetamide (1.202 g, 11.8 mmol) and the reaction mixture was stirred for 6 h at 160° C. under microwave irradiation. After cooling to RT, the volatiles were removed at 40° C. under vacuum and the resulting yellow oil was taken up in a mixture of THF:1 N aq. HCl=1:1 (50 mL) and stirred for 20 min at RT. The volatiles were then removed at 40° C. under vacuum and the residue was then neutralised with a 10 N aqueous NaOH solution. THF was then evaporated before extraction with CH2Cl2 (100 mL). The separated organic layer was washed with brine (20 mL), dried over MgSO4, filtered, and concentrated under vacuum to give N-(2-(6-(cyclopropylmethoxy)-3-formylquinolin-2-ylamino)ethyl)acetamide SLA 47092 as a yellow solid (365 mg, 38% yield).

후처리

  1. temperatureAfter cooling to RT
  2. customthe volatiles were removed at 40° C. under vacuum
  3. additionthe resulting yellow oil was taken up in a mixture of THF
  4. stirring1 N aq. HCl=1:1 (50 mL) and stirred for 20 min at RT
  5. customThe volatiles were then removed at 40° C. under vacuum
  6. customTHF was then evaporated before extraction with CH2Cl2 (100 mL)
  7. washThe separated organic layer was washed with brine (20 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-cffaf4c585ad4a39b2b91677652f6cd7
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772316B2

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