Diisopropylethylamine → N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-(2,5-dimethoxybenzyl)-1,2,4-oxadiazole-3-carboxamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:4]=1[CH2:5][C:6]1[O:10][N:9]=[C:8]([C:11]([O:13]CC)=O)[N:7]=1.Cl.[Cl:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][CH:28]=[C:27]2[CH2:33][CH2:34][NH2:35].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>CO.[OH-].[Na+].O.CN(C=O)C>[Cl:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][CH:28]=[C:27]2[CH2:33][CH2:34][NH:35][C:11]([C:8]1[N:7]=[C:6]([CH2:5][C:4]2[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:3]=2[O:2][CH3:1])[O:10][N:9]=1)=[O:13]Participants
9
Reactant 4
HCID 81531Diisopropylethylamine
HCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochloride
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 66832124Ethyl 5-(2,5-dimethoxybenzyl)-1,2,4-oxadiazole-3-carboxylateProduct 1
Reagents, catalysts & solvents 4
Procedure
This compound was prepared according to method F with ethyl 5-(2,5-dimethoxybenzyl)-1,2,4-oxadiazole-3-carboxylate (0.126 g; 0.433 mmol) in methanol (1 mL) and sodium hydroxide in water (2M, 1 mL); and 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.100 g; 0.433 mmol), HATU (0.164 g; 0.432 mmol), N,N diisopropylethylamine (0.075 mL; 0.432 mmol), in DMF (4 mL). The crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.069 g (36%) of the N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-(2,5-dimethoxybenzyl)-1,2,4-oxadiazole-3-carboxamide as a white solid.
Workup
- customThis compound was prepared
- customThe crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane)
Sources & evidence
- ORD record
- ord-d9bc744e71ab4a8783cc1d0bc926dda0
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434722B2
Reaction notes
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