Diisopropylethylamine → N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-(thiophen-3-ylmethyl)-1,2,4-oxadiazole-3-carboxamide
Reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([CH2:6][C:7]2[O:11][N:10]=[C:9]([C:12]([O:14]CC)=O)[N:8]=2)=[CH:2]1.Cl.[Cl:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[C:22]2[CH2:28][CH2:29][NH2:30].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>C1COCC1.[OH-].[Na+].O.CN(C=O)C>[Cl:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[C:22]2[CH2:28][CH2:29][NH:30][C:12]([C:9]1[N:8]=[C:7]([CH2:6][C:3]2[CH:4]=[CH:5][S:1][CH:2]=2)[O:11][N:10]=1)=[O:14]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 63382666Ethyl 5-[(thiophen-3-yl)methyl]-1,2,4-oxadiazole-3-carboxylateProduct 1
Reagents, catalysts & solvents 4
Procedure
This compound was prepared according to method F with ethyl 5-(thiophen-3-ylmethyl)-1,2,4-oxadiazole-3-carboxylate (0.103 g; 0.433 mmol) in THF (1 mL) and sodium hydroxide in water (2M, 1 mL); 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 (0.186 mL; 1.08 mmol), in DMF (4 mL). The crude mixture was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) and preparative HPLC method 2 to yield 0.0487 g (29%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-(thiophen-3-ylmethyl)-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) and preparative HPLC method 2
Sources & evidence
- ORD record
- ord-e5dd020436894086b7dba2412e16ba7d
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434722B2
Reaction notes
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