1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 5-(1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine

HRID 634088Notes

Reaction equation

HRID 634088 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([NH:12][NH:13][C:14](=S)[NH:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CCN=C=NCCCN(C)C.Cl>C1(C)C=CC=CC=1>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[O:11][C:14]([NH:15][CH2:16][C:17]4[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=4)=[N:13][N:12]=3)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

4

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 867250872-(1H-indole-5-carbonyl)-N-(4-methoxybenzyl)hydrazinecarbothioamide

Product 1

HCID 867250885-(1H-indol-5-yl)-N-(4-methoxybenzyl)-1,3,4-oxadiazol-2-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-(1H-indole-5-carbonyl)-N-(4-methoxybenzyl)hydrazinecarbothioamide (0.1 g, 0.284 mmol) and EDC.HCl (0.109 g, 0.586 mmol) in toluene (10 mL) was heated to reflux for 12 h. The mixture was cooled to RT. The supernatant layer was decanted and the sticky material in the bottom was dissolved in EtOAc (20 mL). The organic layer was washed with water, brine, dried, filtered and concentrated to give the crude material. MS (ESI, pos. ion) m/z: 321 (M+1).

Workup

  1. temperatureto reflux for 12 h
  2. customThe supernatant layer was decanted
  3. dissolutionthe sticky material in the bottom was dissolved in EtOAc (20 mL)
  4. washThe organic layer was washed with water, brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-29d11e47197c49f99617f81c3a35131e
Source dataset
uspto-grants-2016_04
Patent number
US09321756B2

Reaction notes

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