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4-Methylmorpholine → HCID 86753454、化合物

HRID 1458376
ノート
印刷プレビュー

反応式

HRID 1458376 の反応式
[C:1]([O:5][C:6]([N:8]([CH2:31][CH2:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=1)[CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20](O)=[O:21])[CH:18]=2)[NH:13][C:12]=1[C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[CH:24]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O[N:42]1[C:46]2C=CC=CC=2N=N1.Cl.CN[O:54][CH3:55].Cl.CN(C)CCCN=C=NCC.CN1CCOCC1>>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20](=[O:21])[NH:42][CH2:46][O:54][CH3:55])[CH:18]=2)[NH:13][C:12]=1[C:23]1[CH:28]=[C:27]([CH3:29])[CH:26]=[C:25]([CH3:30])[CH:24]=1)[CH2:31][CH2:32][CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=1)([CH3:3])([CH3:4])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 79724-MethylmorpholineHCID 757711-Hydroxybenzotriazole2 回HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)2 回HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2 回HCID 221008763-{2-[tert-butoxycarbonyl-(4-pyridin-4-yl-butyl)amino]ethyl}-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid

生成物 1

HCID 86753454HCID 86753454、化合物収率 90.1%

実験手順

To a solution of 3-{2-[tert-butoxycarbonyl-(4-pyridin-4-yl-butyl)amino]ethyl}-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid (1.44 g in 25 mL N,N-dimethylformamide) at 0° C. was added 540 mg of 1-hydroxybenzotriazole (HOBt) followed by 0.44 mL 4-methylnorpholine and 365 mg N,O-dimethylhydroxylamine hydrochloride. After 15 minutes, 815 mg 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) was added and the mixture allowed to warm to room temperature. After 3 days reaction time, an additional portion of 540 mg of HOBt, 0.44 mL 4-methylmorpholine, 365 mg N,O-dimethylhydroxylamine hydrochloride and 815 mg EDC were added. The reaction stopped after 4 days by concentration in vacuo and reconcentration from toluene to remove all volatiles. The residue was solvated in ethyl acetate and washed sequentially with saturated aqueous sodium bicarbonate and brine, then dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (hexane:ethyl acetate, 30:70; then 20:80; then 0:100) gave the title compound (1.4 g).

後処理

  1. customAfter 3 days reaction time
  2. concentrationThe reaction stopped after 4 days by concentration in vacuo and reconcentration from toluene
  3. customto remove all volatiles
  4. washwashed sequentially with saturated aqueous sodium bicarbonate and brine
  5. dry with materialdried over sodium sulfate
  6. customPurification of the
  7. concentrationconcentrate by flash chromatography on silica gel (hexane

出典と根拠

ORDレコード
ord-50ef092968b14bb2a12713178dd11fed
出典データセット
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05849764

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート