Diisopropylethylamine → N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-4-(3-fluorophenylamino)benzamide

HRID 1777701노트

반응식

HRID 1777701 반응식
[F:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.Cl.[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[C:23]2[CH2:29][CH2:30][NH2:31].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[Cl:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[C:23]2[CH2:29][CH2:30][NH:31][C:13](=[O:15])[C:12]1[CH:11]=[CH:10][C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)=[CH:17][CH:16]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 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 113906104-(3-Fluorophenylamino)benzoic acid

생성물 1

HCID 67974495N-(2-(5-Chloro-1H-indol-3-yl)ethyl)-4-(3-fluorophenylamino)benzamide수율 39%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 4-(3-fluorophenylamino)benzoic acid (0.040 g, 0.173 mmol), 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.040 g; 0.173 mmol), HATU (0.072 g; 0.190 mmol) and N,N-diisopropylethylamine (0.075 mL; 0.432 mmol) in DMF (3 mL), was stirred at room temperature overnight. The reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulfate, the organic layer was washed with sodium carbonate, brine, dried and concentrated under reduced pressure. The crude mixture was purified by flash chromatography on silica (eluent 1 to 10% ethyl acetate in dichloromethane) to yield 0.027 g (39%) of the title compound as a colourless solid.

후처리

  1. customThe reaction mixture was partitioned between ethyl acetate and sodium hydrogen sulfate
  2. washthe organic layer was washed with sodium carbonate, brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe crude mixture was purified by flash chromatography on silica (eluent 1 to 10% ethyl acetate in dichloromethane)

출처 및 근거

ORD 기록
ord-d1d4113f77d247cfb5d10606a2a7cb17
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09266832B2

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