Ethyl Acetate → HCID 66832068, compound

HRID 58686Notes

Reaction equation

HRID 58686 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][NH2:14].CN(C([O:22][N:23]1N=N[C:25]2[CH:26]=[CH:27][CH:28]=N[C:24]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:39](N(CC)C(C)C)(C)C.[C:48](OCC)(=[O:50])C>CN(C=O)C.ClCCl>[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][NH:14][C:48]([C:24]1[CH:25]=[C:26]([CH:27]2[CH2:28][CH2:39]2)[O:22][N:23]=1)=[O:50]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 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)

Product 1

HCID 66832068HCID 66832068, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

This compound was prepared following Method A starting from 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.080 g; 0.339 mmol), intermediate 16 (5-cyclopropylisoxazole-3-carboxylic acid) (0.062 g; 0.407 mmol), HATU (0.155 g; 0.407 mmol) and N,N-diisopropylethylamine (0.112 g; 0.848 mmol) in DMF (3 mL). Flash chromatography on silica gel eluting with 1 to 10% of ethyl acetate in dichloromethane furnished 0.092 g (82%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-cyclopropylisoxazole-3-carboxamide as a solid.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-674939dc1ef04868acfae742f53955d0
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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