Phosgene → 2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-(3-ethylureido)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester

HRID 1857600ノート

反応式

HRID 1857600 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[CH2:17][CH2:18][O:19][C:20]1[C:29]2[C:24](=[CH:25][C:26]([Cl:31])=[C:27]([NH2:30])[CH:28]=2)[NH:23][C:22](=[O:32])[C:21]=1[C:33]1[CH:38]=[C:37]([CH3:39])[CH:36]=[C:35]([CH3:40])[CH:34]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:41](Cl)(Cl)=[O:42].[CH2:45]([N:47](CC)CC)[CH3:46].Cl.C(N)C>C(Cl)Cl.C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[CH2:17][CH2:18][O:19][C:20]1[C:29]2[C:24](=[CH:25][C:26]([Cl:31])=[C:27]([NH:30][C:41]([NH:47][CH2:45][CH3:46])=[O:42])[CH:28]=2)[NH:23][C:22](=[O:32])[C:21]=1[C:33]1[CH:38]=[C:37]([CH3:39])[CH:36]=[C:35]([CH3:40])[CH:34]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 4

HCID 6371PhosgeneHCID 8471Triethylamine2 回HCID 11198Ethylamine hydrochlorideHCID 539323332-{2-[6-Amino-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester

生成物 1

HCID 538466182-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-(3-ethylureido)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2-{2-[6-amino-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester (prepared essentially as described in Example 6, 158 mg in 4 mL dry methylene chloride) at 0° C. was added phosgene (0.22 mL of a 1.93 M solution in toluene) followed by 0.081 mL of triethylamine and the mixture stirred for 1 hour at 0° C. At this time, 114.5 mg of ethylamine hydrochloride was added followed by additional triethylamine (0.195 mL) and the mixture allowed to warm to room temperature. After 20 hours, the mixture was diluted with ethyl acetate (200 mL) and the reaction quenched by the addition of water. The organic portion was washed sequentially with saturated sodium bicarbonate and brine. The solvent was removed in vacuo to provide the crude title compound (187 mg).

後処理

  1. customat 0° C.
  2. temperatureto warm to room temperature
  3. waitAfter 20 hours
  4. customthe reaction quenched by the addition of water
  5. washThe organic portion was washed sequentially with saturated sodium bicarbonate and brine
  6. customThe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-5ec943f57d2c4e8199bad562a26ea036
出典データセット
uspto-grants-2000_11
特許番号
US06147088

反応ノート

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