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

HRID 1777693Notes

Reaction equation

HRID 1777693 reaction equation
[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

Participants

5

Reactant 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-Anilinobenzoic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-5d68241c1e794885b7e49bb11d5b0282
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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