Triethylamine → 3-[3-(4-Fluoro-phenyl)-5-methyl-isoxazole-4-carbonyl]-1H-indole-6-carboxylic acid cyclopropylmethyl-amide

HRID 2224656노트

반응식

HRID 2224656 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]([C:15]3[C:23]4[C:18](=[CH:19][C:20]([C:24](O)=[O:25])=[CH:21][CH:22]=4)[NH:17][CH:16]=3)=[O:14])=[C:11]([CH3:27])[O:10][N:9]=2)=[CH:4][CH:3]=1.CN(C)CCCN=C=NCC.O[N:40]1[C:44]2[CH:45]=[CH:46][CH:47]=CC=2N=N1.CCN(CC)CC.C1(N)CC1>CN(C=O)C>[CH:45]1([CH2:44][NH:40][C:24]([C:20]2[CH:19]=[C:18]3[C:23]([C:15]([C:13]([C:12]4[C:8]([C:5]5[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=5)=[N:9][O:10][C:11]=4[CH3:27])=[O:14])=[CH:16][NH:17]3)=[CH:22][CH:21]=2)=[O:25])[CH2:47][CH2:46]1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 691119953-[3-(4-Fluoro-phenyl)-5-methyl-isoxazole-4-carbonyl]-1H-indole-6-carboxylic acid

생성물 1

HCID 161183293-[3-(4-Fluoro-phenyl)-5-methyl-isoxazole-4-carbonyl]-1H-indole-6-carboxylic acid cyclopropylmethyl-amide수율 72%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 62 mg (0.17 mmol) 3-[3-(4-fluoro-phenyl)-5-methyl-isoxazole-4-carbonyl]-1H-indole-6-carboxylic acid, 41 mg (0.21 mmol) N-(3-dimethylaminopropyl)-N′-ethyl carbodiimide, 23 mg (0.17 mmol) 1-hydroxy benzotriazole, 59 uL (0.43 mmol) Et3N and 0.26 mmol cyclopropylamine in DMF (1 mL) was reacted at room temperature overnight. After evaporation the mixture was subjected to preparative HPLC purification on reversed phase eluting with an acetonitrile/water (0.05% NEt3) gradient to afford 51 mg of the title compound in 72% yield as a white solid. (m/e): 418.1 (MH+; 100%).

후처리

  1. customAfter evaporation the mixture
  2. customwas subjected to preparative HPLC purification on reversed phase
  3. washeluting with an acetonitrile/water (0.05% NEt3) gradient

출처 및 근거

ORD 기록
ord-d74bef7e6baf42ceab5e482f5b0bbeb3
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07378435B2

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