Réaction #53369

Équation de réaction

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

4-(4-hydroxyphenyl)butylamine hydrobromide

4-(4-Hydroxyphenyl)butylamine hydrobromide

→

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

Solvants

THF

triethylamine

Conditions de réaction

Traitement

1. 1
   Températureat reflux temperature for 3 h
2. 2
   Autrethe supernatant was separated
3. 3
   Autrethe solvent was removed under reduced pressure
4. 4
   LavageThe oily residue was washed with water (2×30 mL), ether (3×30 mL)
5. 5
   workup.ADDITION10% HCl (40 mL) was added
6. 6
   workup.STIRRINGThe mixture was vigorously stirred for 10 min
7. 7
   Filtrationthe yellow solid was filtered off
8. 8
   Autredried
9. 9
   Autrerecrystallized twice from ethanol
10. 10
    Autreto give 181 mg (41%) of V as yellow solid

Mode opératoire

1-(3,5-Diamino-6-chloropyrazinoyl-2-methyl-pseudothiourea hydroiodide (0.4 g, 1.03 mmol) was added to a suspension of 4-(4-hydroxyphenyl)butylamine hydrobromide (IV) in a mixture of THF (35 mL) and triethylamine (3 mL). The reaction mixture was stirred at reflux temperature for 3 h, then the supernatant was separated and the solvent was removed under reduced pressure. The oily residue was washed with water (2×30 mL), ether (3×30 mL) and then 10% HCl (40 mL) was added. The mixture was vigorously stirred for 10 min then the yellow solid was filtered off, dried and recrystallized twice from ethanol to give 181 mg (41%) of V as yellow solid. Purity is 98% by HPLC, retention time is 9.77 min; 1H NMR (300 MHz, DMSO-d6) δ1.56 (br s, 4H), 2.48 (br s, 2H), 3.35 (m, 2H), 6.65 (d, J=8.5 Hz, 2H), 6.95 (d, J=8.6 Hz, 2H), 7.50 (br s, 2H), 8.75 (br s, 1H), 9.05 (br .s, 1H), 9.33 (br s, 2H), 10.55 (s, 1H); 13C NMR (75 MHz, CD3OD) 28.7, 29.8, 35.4, 42.4, 111.2, 116.1, 122.0, 130.0, 134.0, 155.0, 156.1, 156.8, 157.5, 167.0; APCI MS m/z=378 [C16H20ClN7O2+H]+.

Source