Phenyl chloroformate → Phenyl [5-cyano-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carbamate

HRID 57194ノート

反応式

HRID 57194 の反応式
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[NH2:11][C:12]1([C:38]2[C:39]([O:44][CH2:45][CH3:46])=[N:40][CH:41]=[CH:42][CH:43]=2)[C:20]2[C:15](=[CH:16][C:17]([F:23])=[C:18]([C:21]#[N:22])[CH:19]=2)[N:14]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=2[O:35][CH3:36])(=[O:26])=[O:25])[C:13]1=[O:37]>N1C=CC=CC=1>[C:21]([C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][C:17]=1[F:23])[N:14]([S:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=1[O:35][CH3:36])(=[O:25])=[O:26])[C:13](=[O:37])[C:12]2([NH:11][C:2](=[O:3])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:38]1[C:39]([O:44][CH2:45][CH3:46])=[N:40][CH:41]=[CH:42][CH:43]=1)#[N:22]

参加物

4

反応物 2

HCID 15891Phenyl chloroformateHCID 670877293-Amino-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile

生成物 1

HCID 86725451Phenyl [5-cyano-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carbamate収率 71.9%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

61 μl (0.49 mmol) of phenyl chloroformate were slowly added dropwise to a solution, cooled to 0° C., of 226 mg (0.44 mmol) of 3-amino-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile in 4 ml of pyridine. After 5 minutes, the solvent was evaporated. The residue was mixed with 20 ml of water and extracted with diethyl ether (2×). The organic phase was washed with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (Redisep cartridge, mobile phase gradient from 0 to 5% methanol in ethyl acetate). 200 mg of the title compound were obtained.

後処理

  1. customthe solvent was evaporated
  2. additionThe residue was mixed with 20 ml of water
  3. extractionextracted with diethyl ether (2×)
  4. washThe organic phase was washed with water and saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel (Redisep cartridge, mobile phase gradient from 0 to 5% methanol in ethyl acetate)

出典と根拠

ORDレコード
ord-1ed35a49a8474c459235ac9e3e48e4d7
出典データセット
uspto-grants-2016_09
特許番号
US09434713B2

反応ノート

読み込み中…