4-(4-aminobutyl)phenol Hydrobromide → 4-(4-Hydroxyphenyl)butylamidino-3,5-diamino-6-chloropyrazinecarboxamide hydrochloride

HRID 457592Notes

Reaction equation

HRID 457592 reaction equation
I.[NH2:2][C:3]1[C:4]([C:11]([NH:13][C:14](=[NH:17])SC)=[O:12])=[N:5][C:6]([Cl:10])=[C:7]([NH2:9])[N:8]=1.Br.[OH:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][CH2:28][CH2:29][NH2:30])=[CH:22][CH:21]=1>C1COCC1.C(N(CC)CC)C>[ClH:10].[OH:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:26][CH2:27][CH2:28][CH2:29][NH:30][C:14]([NH:13][C:11]([C:4]2[C:3]([NH2:2])=[N:8][C:7]([NH2:9])=[C:6]([Cl:10])[N:5]=2)=[O:12])=[NH:17])=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 115505224-(4-aminobutyl)phenol HydrobromideHCID 140329753methyl N-(3,5-diamino-6-chloropyrazine-2-carbonyl)carbamimidothioate;hydroiodide

Product 1

HCID 1784793374-(4-Hydroxyphenyl)butylamidino-3,5-diamino-6-chloropyrazinecarboxamide hydrochlorideYield 84.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

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 (4) (0.8 g, 32 mmol) in a mixture of THF (35 mL) and triethylamine (3 mL). The reaction mixture was stirred in the boiling solvent 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 5 (0.18 g, 41%) as yellow solid. Purity is 98% by HPLC, retention time is 9.77 min. 1H NMR (300 MHz, DMSO-d6) δ 1.56 (br s, 4H), 2.48 (br s, 2H), 3.35 (m, 2H), 6.65 (d, 2H), 6.95 (d, 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]+.

Workup

  1. customthe supernatant was separated
  2. customthe solvent was removed under reduced pressure
  3. washThe oily residue was washed with water (2×30 mL), ether (3×30 mL)
  4. addition10% HCl (40 mL) was added
  5. stirringThe mixture was vigorously stirred for 10 min
  6. filtrationthe yellow solid was filtered off
  7. customdried
  8. customrecrystallized twice from ethanol

Sources & evidence

ORD record
ord-bbdbef4073cb470a8eb83f8efa90b452
Source dataset
uspto-grants-2007_03
Patent number
US07189719B2

Reaction notes

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