Triethylamine → Rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-yl]-piperidine-1-carboxylic acid methylamide

HRID 2102697ノート

反応式

HRID 2102697 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)([CH:12]3[CH2:17][CH2:16][CH2:15][NH:14][CH2:13]3)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[N:33]([CH3:36])=[C:34]=[O:35]>ClCCl>[CH3:36][NH:33][C:34]([N:14]1[CH2:15][CH2:16][CH2:17][CH:12]([C:6]2([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)[C:5]3[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=3)[NH:8][C:7]2=[O:11])[CH2:13]1)=[O:35]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 57803070Rac-6-chloro-3-(3-chloro-benzyl)-3-piperidin-3-yl-1,3-dihydro-indol-2-one

生成物 1

HCID 11998150Rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-yl]-piperidine-1-carboxylic acid methylamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of rac-6-chloro-3-(3-chloro-benzyl)-3-piperidin-3-yl-1,3-dihydro-indol-2-one (80 mg, 0.2 mmol) (from Example 25a supra) in dichloromethane (2 mL) was added triethylamine (32.4 mg, 0.3 mmol) (Aldrich), followed by the addition of isocyanatomethane (14.6 mg, 0.24 mmol) (Chem Service). The mixture was stirred at room temperature for 30 minutes. The mixture was then partitioned between ethyl acetate and water. The aqueous layer was extracted with another two portions of ethyl acetate. The combined organic layers were washed with water, brine, dried over Na2SO4 and concentrated. The residue was triturated with dichloromethane-hexanes to give rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperidine-1-carboxylic acid methylamide as a white solid. (Yield 35 mg, 50%).

後処理

  1. customThe mixture was then partitioned between ethyl acetate and water
  2. extractionThe aqueous layer was extracted with another two portions of ethyl acetate
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was triturated with dichloromethane-hexanes

出典と根拠

ORDレコード
ord-272636731342484684d42535ceba92a9
出典データセット
uspto-grants-2009_08
特許番号
US07576082B2

反応ノート

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