Pyridine → 2-{2-[3-(3-Bromophenyl)-7-chloro-6-(3-cyclopropyl-ureido)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1857618노트

반응식

HRID 1857618 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:28])=[C:24]([NH2:27])[CH:25]=2)[NH:20][C:19](=[O:29])[C:18]=1[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([Br:36])[CH:31]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:37]1[CH:42]=C[CH:40]=[CH:39][CH:38]=1.ClC(Cl)([O:46]C(=O)OC(Cl)(Cl)Cl)Cl.C1(N)CC1>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:28])=[C:24]([NH:27][C:42]([NH:37][CH:38]3[CH2:40][CH2:39]3)=[O:46])[CH:25]=2)[NH:20][C:19](=[O:29])[C:18]=1[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([Br:36])[CH:31]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 69828CyclopropylamineHCID 94429TriphosgeneHCID 541646722-{2-[6-Amino-3-(3-bromophenyl)-7-chloro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 539044082-{2-[3-(3-Bromophenyl)-7-chloro-6-(3-cyclopropyl-ureido)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To a solution of 2-{2-[6-amino-3-(3-bromophenyl)-7-chloro-2-oxo-1,2-dihydroquinolin-4-yloxy]-1-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (20 mg in 1.0 mL methylene chloride) at 0° C. was added 0.009 mL pyridine followed by 4 mg triphosgene and the mixture allowed to stir at 0° C. for 1 hour. At this time 0.012 mL of cyclopropylamine was added via syringe and the reaction mixture warmed to room temperature. After 2 hours, the mixture was diluted with 20 mL ethyl acetate and washed with saturated ammonium chloride (10 mL) and brine (10 mL). The organic portion was dried over magnesium sulfate then concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (hexane:ethyl acetate, 2:1; then 1:1; then 0:1) to give the title compound (14 mg).

후처리

  1. temperaturethe reaction mixture warmed to room temperature
  2. waitAfter 2 hours
  3. washwashed with saturated ammonium chloride (10 mL) and brine (10 mL)
  4. dry with materialThe organic portion was dried over magnesium sulfate
  5. concentrationthen concentrated in vacuo
  6. customThe crude product was purified by flash chromatography on silica gel (hexane

출처 및 근거

ORD 기록
ord-91f094319816460da755ca68ef4b0d9c
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06147088

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