1-[(2-methyl-5,8-dihydro-4-quinolinyl)methyl]-1H-indole-5-carbonyl chloride → 1-tert-butyl 3-methyl 4-[({1-[(2-methyl-4-quinolinyl)methyl]-1H-indol-5-yl}carbonyl)amino]-1,3-pyrrolidinedicarboxylate

HRID 351966ノート

反応式

HRID 351966 の反応式
[NH2:1][CH:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4][CH:3]1[C:14]([O:16][CH3:17])=[O:15].[CH3:18][C:19]1[CH:28]=[C:27]([CH2:29][N:30]2[C:38]3[C:33](=[CH:34][C:35]([C:39](Cl)=[O:40])=[CH:36][CH:37]=3)[CH:32]=[CH:31]2)[C:26]2[CH2:25][CH:24]=[CH:23][CH2:22][C:21]=2[N:20]=1>C(Cl)Cl.O>[CH3:18][C:19]1[CH:28]=[C:27]([CH2:29][N:30]2[C:38]3[C:33](=[CH:34][C:35]([C:39]([NH:1][CH:2]4[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4][CH:3]4[C:14]([O:16][CH3:17])=[O:15])=[O:40])=[CH:36][CH:37]=3)[CH:32]=[CH:31]2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1

参加物

5

反応物 2

HCID 222583801-[(2-methyl-5,8-dihydro-4-quinolinyl)methyl]-1H-indole-5-carbonyl chlorideHCID 235906351-tert-Butyl 3-methyl 4-aminopyrrolidine-1,3-dicarboxylate

生成物 1

HCID 222584971-tert-butyl 3-methyl 4-[({1-[(2-methyl-4-quinolinyl)methyl]-1H-indol-5-yl}carbonyl)amino]-1,3-pyrrolidinedicarboxylate収率 70%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

The 1-tert-butyl 3-methyl 4-amino-1,3-pyrrolidinedicarboxylate (0.10 g, 0.41 mmol) was combined with the acid chloride from step (501b) (0.10 g, 0.32 mmol) in methylene chloride (15 mL) and water saturated sodium bicarbonate (15 mL). The reaction was stirred for 3.5 h, partitioned between methylene chloride and water. The organic layer was washed with brine, dried over magnesium sulfate and concentrated to give a solid. This was purified by flash chromatography on silica gel eluting hexane: ethyl acetate (30:60, v:v) to give the 1-tert-butyl 3-methyl 4-[({1-[(2-methyl-4-quinolinyl)methyl]-1H-indol-5-yl}carbonyl)amino]-1,3-pyrrolidinedicarboxylate (0.120 g, 70%) as a solid, MS (M+H)+=543.

後処理

  1. custompartitioned between methylene chloride and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give a solid
  6. customThis was purified by flash chromatography on silica gel
  7. washeluting hexane: ethyl acetate (30:60, v:v)

出典と根拠

ORDレコード
ord-2a55b1d680f6412d919ea174e43e4c21
出典データセット
uspto-grants-2004_06
特許番号
US06743807B2

反応ノート

読み込み中…