Oxalyl chloride → (2-{6-Chloro-3-[4-(2-oxo-2,3-dihydro-indol-1-yl)-piperidine-1-carbonyl]-indol-1-yl}-ethyl)-methyl-carbamic acid tert-butyl ester

HRID 1097843ノート

反応式

HRID 1097843 の反応式
[C:1]([O:5][C:6]([N:8]([CH3:24])[CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:20])[CH:18]=2)[C:13]([C:21]([OH:23])=O)=[CH:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.C(Cl)(=O)C(Cl)=O.[NH:40]1[CH2:45][CH2:44][CH:43]([N:46]2[C:54]3[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=3)[CH2:48][C:47]2=[O:55])[CH2:42][CH2:41]1>CN(C)C=O>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:20])[CH:18]=2)[C:13]([C:21]([N:40]2[CH2:45][CH2:44][CH:43]([N:46]3[C:54]4[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=4)[CH2:48][C:47]3=[O:55])[CH2:42][CH2:41]2)=[O:23])=[CH:12]1)[CH3:24])([CH3:2])([CH3:3])[CH3:4]

参加物

6

反応物 4

HCID 65578Oxalyl chlorideHCID 81531Diisopropylethylamine2 回HCID 27611521-Piperidin-4-yl-1,3-dihydro-2H-indol-2-oneHCID 597567001-[2-(tert-Butoxycarbonyl-methyl-amino)-ethyl]-6-chloro-1H-indole-3-carboxylic acid

生成物 1

HCID 66811008(2-{6-Chloro-3-[4-(2-oxo-2,3-dihydro-indol-1-yl)-piperidine-1-carbonyl]-indol-1-yl}-ethyl)-methyl-carbamic acid tert-butyl ester収率 82.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide触媒

実験手順

To a solution of 0.20 g (0.57 mmol) 1-[2-(tert-butoxycarbonyl-methyl-amino)-ethyl]-6-chloro-1H-indole-3-carboxylic acid, 0.11 ml (0.63 mmol) N,N-diisopropylethylamine and 2 drops of N,N-dimethylformamide in 4 ml dicholormethane were added 0.060 ml (0.74 mmol) oxalyl chloride at 0-5° C. After completed addition the reaction mixture was allowed to warm to room temperature and stirred for 3 h. A solution of 0.15 g (0.68 mmol) 1,3-dihydro-1-(piperidin-4-yl)-(2H)-indol-2-one and 0.11 ml (0.63 mmol) N,N-diisopropylethylamine in 2 ml dicholormethane was added. After stirring for 15 min at room temperature silica gel was added to the reaction mixture and the solvent was evaporated in vacuo. The residue was transferred to a silica gel column. Elution gave 0.26 g (82%) of the title compound as an off-white solid.

後処理

  1. additionaddition the reaction mixture
  2. stirringAfter stirring for 15 min at room temperature silica gel
  3. additionwas added to the reaction mixture
  4. customthe solvent was evaporated in vacuo
  5. washElution

出典と根拠

ORDレコード
ord-8f5119c0dd8f44a9971d61101e507736
出典データセット
uspto-grants-2012_03
特許番号
US08143281B2

反応ノート

読み込み中…