Diisopropylethylamine → HCID 49868777, compound

HRID 58787Notes

Reaction equation

HRID 58787 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].[CH2:15]([O:17][CH2:18][CH:19]1[O:23][N:22]=[C:21]([C:24](O)=[O:25])[CH2:20]1)[CH3:16].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.ClCCl.C(OCC)(=O)C>[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:24]([C:21]1[CH2:20][CH:19]([CH2:18][O:17][CH2:15][CH3:16])[O:23][N:22]=1)=[O:25]

Participants

8

Reactant 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 668317425-(Ethoxymethyl)-4,5-dihydroisoxazole-3-carboxylic acid

Product 1

HCID 49868777HCID 49868777, compoundYield 64.3%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

This compound was prepared following Method A starting from 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.073 g; 0.311 mmol), 5-(ethoxymethyl)-4,5-dihydroisoxazole-3-carboxylic acid (0.054 g; 0.311 mmol), HATU (0.130 g; 0.343 mmol) and N,N-diisopropylethylamine (1.36 mL; 0.779 mmol) in DMF (3 mL). Flash chromatography on silica gel eluting with 1 to 10% of ethyl acetate in dichloromethane gave 0.070 g (64%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-(ethoxymethyl)-4,5-dihydroisoxazole-3-carboxamide as a solid.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-7648ba5fcc984aca8e45f262743001d2
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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