Reacción #53377

Ecuación de reacción

ethyl acetate

Triethylamine

compound 14

3-(4-Hydroxyphenyl)propylamine hydrobromide

3,5-diamino-6-chloropyrazinoyl-2-methyl-pseudothiourea hydroiodide

→

compound 15

Rendimiento 60.0%

3-(4-Hydroxyphenyl)propylamidino-3,5-diamino-6-chloropyrazinecarboxamide hydrochloride

Rendimiento 60.0%

Disolventes

THF

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred
2. 2
   Temperaturaat reflux for 3 h
3. 3
   TemperaturaThe solution was then cooled to room temperature
4. 4
   Otrothe supernatant was isolated
5. 5
   OtroThe solvent was evaporated
6. 6
   Lavadothe residual oil was washed with ether (2×50 mL), ethyl acetate (50 mL)
7. 7
   workup.ADDITIONtreated with 20 ml of 10% HCl
8. 8
   OtroThe obtained solid was isolated by filtration
9. 9
   Otrothe precipitation of a yellow solid
10. 10
    Otrowhich was isolated by centrifugation
11. 11
    Lavadowashed with ethyl acetate
12. 12
    Otrodried under vacuum

Procedimiento

Triethylamine (8 mL) was added to suspension of compound 14 (0.470 g, 2 mmol) in THF (40 mL) and the mixture was stirred at room temperature for 15 min. After this time 1-(3,5-diamino-6-chloropyrazinoyl-2-methyl-pseudothiourea hydroiodide (0.15 g, 0.4 mmol) was added and the mixture was stirred at reflux for 3 h. The solution was then cooled to room temperature and the supernatant was isolated. The solvent was evaporated and the residual oil was washed with ether (2×50 mL), ethyl acetate (50 mL) and treated with 20 ml of 10% HCl. The obtained solid was isolated by filtration and dissolved in MeOH (approx. 50 mL). Addition of ethyl acetate (20 mL) to the solution caused the precipitation of a yellow solid, which was isolated by centrifugation, washed with ethyl acetate and dried under vacuum to give compound 15 (48 mg, 31%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ1.80 (br s, 2H), 2.58 (m, 2H), 3.95 (br s, 4H), 6.70 (d, 2H), 7.03 (d, 2H), 7.48 (br. s, 2H), 8.80 (br s, 1H), 8.93 (br s, 1H), 9.32 (br s, 2H), 10.52 (s, 1H). APCI MS m/z=364 [C15H18ClN7O2+H]+.

Fuente