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

HRID 1851563ノート

反応式

HRID 1851563 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-93285be08ade442abbe3f1734f46afa3
出典データセット
uspto-grants-2015_02
特許番号
US08957070B2

反応ノート

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