Triethylamine → HCID 66831889, compound

HRID 58675Notes

Reaction equation

HRID 58675 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]1([C:21]2[O:25][C:24]([C:26](Cl)=[O:27])=[N:23][N:22]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.C(OCC)(=O)C>ClCCl>[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:26]([C:24]1[O:25][C:21]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)=[N:22][N:23]=1)=[O:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 27796565-Phenyl-1,3,4-oxadiazole-2-carbonyl chlorideHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochloride

Product 1

HCID 66831889HCID 66831889, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

This compound was obtained following Method B starting from 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.0417 g, 0.177 mmol), 5-phenyl-1,3,4-oxadiazole-2-carbonyl chloride (0.041 g; 0.177 mmol), and triethylamine (0.0621 mL; 0.442 mmol) in dichloromethane (3 mL). Flash chromatography on silica gel eluting with 2 to 16% of ethyl acetate in dichloromethane gave 0.0223 g (34%) of N-(2-(5-chloro-1H-indol-3-yl)ethyl)-5-phenyl-1,3,4-oxadiazole-2-carboxamide as a solid.

Workup

  1. customThis compound was obtained

Sources & evidence

ORD record
ord-f6ad9de58cea4e86a7b345dd80f304ac
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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