Trifluoroacetic acid → 1-[2-(4-Aminopiperidin-1-yl)ethyl]-2-oxo-1,2-dihydroquinoline-7-carbonitrile

HRID 1644291노트

반응식

HRID 1644291 반응식
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]#[N:27])[CH:24]=3)[CH:19]=[CH:18][C:17]2=[O:28])[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]#[N:27])[CH:24]=3)[CH:19]=[CH:18][C:17]2=[O:28])[CH2:10][CH2:9]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 60200429tert-butyl 1-(2-(7-cyano-2-oxoquinolin-1(2H)-yl)ethyl)piperidin-4-ylcarbamate2회

생성물 1

HCID 602009201-[2-(4-Aminopiperidin-1-yl)ethyl]-2-oxo-1,2-dihydroquinoline-7-carbonitrile

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of tert-butyl{1-[2-(7-cyano-2-oxoquinolin-1(2H)-yl)ethyl]piperidin-4-yl}carbamate (Intermediate 15) (6.57 g, 16.57 mmol) in dichloromethane (100 mL) was treated with trifluoroacetic acid (40 mL) at 0° C. for 30 minutes. The solvent was removed under reduced pressure and the residue codistilled once with dichloromethane, then taken up in dichloromethane (200 mL) and washed with saturated sodium hydrogencarbonate solution (50 mL, pH adjusted to 10 with sodium hydroxide). The aqueous phase was back-extracted three times with dichloromethane (3×100 mL) and dried over sodium sulfate. The solvent was removed under reduced pressure to give the product as off-white solid, 5 g, mp 138° C.

후처리

  1. customThe solvent was removed under reduced pressure
  2. washwashed with saturated sodium hydrogencarbonate solution (50 mL
  3. extractionThe aqueous phase was back-extracted three times with dichloromethane (3×100 mL)
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-f5bfcaa96adf44888c1e816999f18963
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124602B2

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