Diisopropylethylamine → 5-(4-tert-butylbenzyl)-N-(2-(5-chloro-1H-indol-3-yl)ethyl)-1,2,4-oxadiazole-3-carboxamide
Reaction equation
[C:1]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][C:10]2[O:14][N:13]=[C:12]([C:15]([O:17]CC)=O)[N:11]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].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.CN(C=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][C:10]2[O:14][N:13]=[C:12]([C:15]([NH:35][CH2:34][CH2:33][C:27]3[C:26]4[C:30](=[CH:31][CH:32]=[C:24]([Cl:23])[CH:25]=4)[NH:29][CH:28]=3)=[O:17])[N:11]=2)=[CH:20][CH:21]=1)([CH3:2])([CH3:3])[CH3:4]Participants
7
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 66831957Ethyl 5-(4-tert-butylbenzyl)-1,2,4-oxadiazole-3-carboxylateProduct 1
Reagents, catalysts & solvents 2
Procedure
This compound was prepared according to method F with ethyl 5-(4-tert-butylbenzyl)-1,2,4-oxadiazole-3-carboxylate (0.125 g; 0.433 mmol) in methanol (2 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 0.042 g (22%) of 5-(4-tert-butylbenzyl)-N-(2-(5-chloro-1H-indol-3-yl)ethyl)-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-d38eb36d51444a09bf7f0e8128fa93a1
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434722B2
Reaction notes
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