(S)-2-{2-[7-chloro-6-(3-cyclopropylureido)-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester → (S)-1-[7-chloro-3-(3,5-dimethylphenyl)-2-oxo-4-(2-piperidin-2-yl-ethoxy)-1,2-dihydroquinolin-6-yl]-3-cyclopropylurea

HRID 1857612노트

반응식

HRID 1857612 반응식
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:34])=[C:24]([NH:27][C:28]([NH:30][CH:31]3[CH2:33][CH2:32]3)=[O:29])[CH:25]=2)[NH:20][C:19](=[O:35])[C:18]=1[C:36]1[CH:41]=[C:40]([CH3:42])[CH:39]=[C:38]([CH3:43])[CH:37]=1)=O)(C)(C)C>C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[Cl:34][C:23]1[CH:22]=[C:21]2[C:26]([C:17]([O:16][CH2:15][CH2:14][C@@H:9]3[CH2:10][CH2:11][CH2:12][CH2:13][NH:8]3)=[C:18]([C:36]3[CH:41]=[C:40]([CH3:42])[CH:39]=[C:38]([CH3:43])[CH:37]=3)[C:19](=[O:35])[NH:20]2)=[CH:25][C:24]=1[NH:27][C:28]([NH:30][CH:31]1[CH2:32][CH2:33]1)=[O:29]

참가 물질

4

반응물 1

HCID 53968811(S)-2-{2-[7-chloro-6-(3-cyclopropylureido)-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 44292939(S)-1-[7-chloro-3-(3,5-dimethylphenyl)-2-oxo-4-(2-piperidin-2-yl-ethoxy)-1,2-dihydroquinolin-6-yl]-3-cyclopropylurea수율 87.8%

시약·촉매·용매 2

HCID 7519Anisole촉매HCID 6422Trifluoroacetic acid용매

실험 절차

To a solution of (S)-2-{2-[7-chloro-6-(3-cyclopropylureido)-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (615 mg in 10 mL dry methylene chloride) was added 10 drops of anisole followed by 10 mL of trifluoroacetic acid and the mixture stirred at room temperature. After 1 hour the solvents were removed in vacuo and the resulting residue purified by flash chromatography on silica gel (chloroform:10% ammonium hydroxide in methanol, 90:10) to give the title compound (451 mg).

후처리

  1. customAfter 1 hour the solvents were removed in vacuo
  2. customthe resulting residue purified by flash chromatography on silica gel (chloroform:10% ammonium hydroxide in methanol, 90:10)

출처 및 근거

ORD 기록
ord-eafc48d6dd074798bb77b35b1fa243d2
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06147088

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