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

HRID 1992494노트

반응식

HRID 1992494 반응식
[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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-a88c7cae3c934578a3bb0af1ddd7fc65
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07648979B2

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