1-Hydroxybenzotriazole → 7-[Methyl(2-thienylsulfonyl)amino]-N-[2-(tritylthio)ethyl]-5-(trifluoromethoxy)-1H-indole-2-carboxamide

HRID 1851563노트

반응식

HRID 1851563 반응식
[CH3:1][N:2]([S:20]([C:23]1[S:24][CH:25]=[CH:26][CH:27]=1)(=[O:22])=[O:21])[C:3]1[CH:4]=[C:5]([O:15][C:16]([F:19])([F:18])[F:17])[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([OH:14])=O)=[CH:8]2.Cl.[C:29]([S:48][CH2:49][CH2:50][NH2:51])([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.N1(O)C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>C(OCC)(=O)C.CN(C)C=O.C(N(CC)CC)C>[CH3:1][N:2]([S:20]([C:23]1[S:24][CH:25]=[CH:26][CH:27]=1)(=[O:21])=[O:22])[C:3]1[CH:4]=[C:5]([O:15][C:16]([F:17])([F:18])[F:19])[CH:6]=[C:7]2[C:11]=1[NH:10][C:9]([C:12]([NH:51][CH2:50][CH2:49][S:48][C:29]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)=[O:14])=[CH:8]2

참가 물질

8

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 184272672-(Tritylthio)ethylamine hydrochlorideHCID 574761867-[methyl(2-thienylsulfonyl)amino]-5-(trifluoromethoxy)-1H-indole-2-carboxylic acid

생성물 1

HCID 579017387-[Methyl(2-thienylsulfonyl)amino]-N-[2-(tritylthio)ethyl]-5-(trifluoromethoxy)-1H-indole-2-carboxamide수율 31.1%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 7-[methyl(2-thienylsulfonyl)amino]-5-(trifluoromethoxy)-1H-indole-2-carboxylic acid (0.30 g), 2-(tritylthio)ethylamine hydrochloride (0.32 g), triethylamine (0.13 mL) and N,N-dimethylformamide (10 mL) were added 1H-1,2,3-benzotriazol-1-ol (0.15 g) and N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (0.19 g) under ice-cooling, and the mixture was stirred at room temperature for 18 hr. The reaction solution was diluted with ethyl acetate, washed with water, aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=5:95-20:80), and the obtained crystals were washed with diethyl ether-hexane to give the title compound (160 mg, yield 31%) as colorless crystals. melting point 222-223° C.

후처리

  1. temperaturecooling
  2. washwashed with water, aqueous sodium hydrogencarbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washthe obtained crystals were washed with diethyl ether-hexane

출처 및 근거

ORD 기록
ord-93285be08ade442abbe3f1734f46afa3
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957070B2

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