1-Hydroxybenzotriazole → 5-(4-tert-butoxycarbonyl-[1,4]diazepane-1-carbonyl)-1H-indole-2-carboxylic acid ethyl ester

HRID 1992494ノート

反応式

HRID 1992494 の反応式
[CH3:1][CH2:2][O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]([OH:17])=O)=[CH:10][CH:9]=2)=[O:5].[N:18]1([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[CH2:2]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([C:15]([N:21]1[CH2:22][CH2:23][CH2:24][N:18]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:19][CH2:20]1)=[O:17])=[CH:10][CH:9]=2)=[O:5])[CH3:1]

参加物

6

反応物 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 180713652-(Ethoxycarbonyl)-1H-indole-5-carboxylic acid

生成物 1

HCID 685368405-(4-tert-butoxycarbonyl-[1,4]diazepane-1-carbonyl)-1H-indole-2-carboxylic acid ethyl ester収率 96.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1H-indole-2,5-dicarboxylic acid 2-ethyl ester (3.08 g, 13 mmol) and tert-butyl 1-homopiperazine-carboxylate (1 eq., 2.657 g) in DMF (50 ml) was added N-hydroxybenzotriazole (0.2 eq., 360 mg). After a five minutes, N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide hydrochloride (1.2 eq., 3.05 g) was added and the mixture stirred at room temperature overnight. The solvent was removed under reduced pressure and the crude product was purified by column chromatography on silica gel (3:1 heptane/ethyl acetate eluant) to afford the product as a light-brown solid (5.21 g, 94%). MS (m/z): 416.4 (M+H)+.

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe crude product was purified by column chromatography on silica gel (3:1 heptane/ethyl acetate eluant)

出典と根拠

ORDレコード
ord-a88c7cae3c934578a3bb0af1ddd7fc65
出典データセット
uspto-grants-2010_01
特許番号
US07648979B2

反応ノート

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