Diisopropylethylamine → tert-butyl 3-(2-(5-chloro-1H-indol-3-yl)ethylcarbamoyl)isoxazol-5-ylcarbamate

HRID 58684Notes

Reaction equation

HRID 58684 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].[C:15]([O:19][C:20]([NH:22][C:23]1[O:27][N:26]=[C:25]([C:28](O)=[O:29])[CH:24]=1)=[O:21])([CH3:18])([CH3:17])[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:28]([C:25]1[CH:24]=[C:23]([NH:22][C:20](=[O:21])[O:19][C:15]([CH3:17])([CH3:16])[CH3:18])[O:27][N:26]=1)=[O:29]

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 668320051258503-55-7

Product 1

HCID 66831951tert-butyl 3-(2-(5-chloro-1H-indol-3-yl)ethylcarbamoyl)isoxazol-5-ylcarbamateYield 94.5%

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 (0.505 g; 2.14 mmol), the INTERMEDIATE 14: 5-(tert-butoxycarbonylamino)isoxazole-3-carboxylic acid (0.513 g; 2.25 mmol), HATU (0.896 g; 2.36 mmol) and N,N-diisopropylethylamine (0.935 mL; 5.35 mmol) in DMF (5 mL). Flash chromatography on silica gel eluting with 2 to 20% of ethyl acetate in dichloromethane afforded 0.819 g (94%) of tert-butyl 3-(2-(5-chloro-1H-indol-3-yl)ethylcarbamoyl)isoxazol-5-ylcarbamate as a white solid.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-6ace8545c4ee484cbba5a5c796ab507b
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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