5-Chloro-1H-indole-3-ethylamine monohydrochloride → N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-3-(phenylamino)benzamide

HRID 1777693노트

반응식

HRID 1777693 반응식
[C:1]1([NH:7][C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=2)[C:11]([OH:13])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[Cl:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[C:22]2[CH2:28][CH2:29][NH2:30].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Cl:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[C:22]2[CH2:28][CH2:29][NH:30][C:11](=[O:13])[C:10]1[CH:14]=[CH:15][CH:16]=[C:8]([NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:9]=1

참가 물질

5

반응물 3

HCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 128503413-(Phenylamino)benzoic acid

생성물 1

HCID 71451287N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-3-(phenylamino)benzamide수율 25.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 3-(phenylamino)benzoic acid (0.155 g, 0.727 mmol), 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.168 g; 0.727 mmol), HATU (0.303 g; 0.799 mmol) and N,N-diisopropylethyldiamine (0.313 mL; 1.82 mmol) in DMF (5 mL), was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulphate, the organic layer was washed with sodium carbonate, brine, dried and concentrated in vacuo. The crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.072 g (25%) of the title compound as a pink solid.

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulphate
  2. washthe organic layer was washed with sodium carbonate, brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-5d68241c1e794885b7e49bb11d5b0282
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266832B2

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