Dimethylformamide → 2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(pyrimidin-4-ylcarbamoyl)-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1858092ノート

反応式

HRID 1858092 の反応式
[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](I)[CH:25]=2)[NH:20][C:19](=[O:29])[C:18]=1[C:30]1[CH:35]=[C:34]([CH3:36])[CH:33]=[C:32]([CH3:37])[CH:31]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:38][C:39]1[CH:44]=[CH:43][N:42]=[CH:41][N:40]=1.CN(C)[CH:47]=[O:48]>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[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]([C:47](=[O:48])[NH:38][C:39]3[CH:44]=[CH:43][N:42]=[CH:41][N:40]=3)[CH:25]=2)[NH:20][C:19](=[O:29])[C:18]=1[C:30]1[CH:35]=[C:34]([CH3:36])[CH:33]=[C:32]([CH3:37])[CH:31]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 689584-AminopyrimidineHCID 539972552-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-iodo-2-oxo-1,2-dihydro-quinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 537223102-{2-[7-Chloro-3-(3,5-dimethylphenyl)-2-oxo-6-(pyrimidin-4-ylcarbamoyl)-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 8471Triethylamine溶媒

反応条件

温度
90 °C

実験手順

To a suspension of 2-{2-[7-chloro-3-(3,5-dimethylphenyl)-6-iodo-2-oxo -1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (0.10 g in a mixture of 1 mL N,N-dimethylformamide and 0.04 mL triethylamine) was added 75 mg of 4-aminopyrimidine followed by 0.8 mg dichlorobis(triphenylphosphine)palladium(II) and the flask flushed (5×) with carbon monoxide. The mixture was then heated to 90° C. on an oil bath under a carbon monoxide atmosphere. After 16 hours, the mixture was cooled to room temperature, diluted with ethyl acetate and washed with water and brine. The organic portion was dried over sodium sulfate and concentrated in vacuo. Purification by flash chromatography on silica gel (ethyl acetate:hexane, 35:65; then methylene chloride:methanol, 95:5) gave the title compound (70 mg).

後処理

  1. customthe flask flushed (5×) with carbon monoxide
  2. temperaturethe mixture was cooled to room temperature
  3. additiondiluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialThe organic portion was dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel (ethyl acetate

出典と根拠

ORDレコード
ord-abb56d654a5c4ba1b1e452b9c519ddaf
出典データセット
uspto-grants-2000_11
特許番号
US06150352

反応ノート

読み込み中…