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4-Methylmorpholine → HCID 86753454, 화합물

HRID 1458376
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HRID 1458376 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 5

HCID 79724-MethylmorpholineHCID 757711-Hydroxybenzotriazole2회HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)2회HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2회HCID 221008763-{2-[tert-butoxycarbonyl-(4-pyridin-4-yl-butyl)amino]ethyl}-2-(3,5-dimethylphenyl)-1H-indole-5-carboxylic acid

생성물 1

HCID 86753454HCID 86753454, 화합물수율 90.1%

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-50ef092968b14bb2a12713178dd11fed
출처 데이터셋
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05849764

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