4-(5-Aminopentyl)phenol → HCID 178479342, compound

HRID 458579Notes

Reaction equation

HRID 458579 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.[OH:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][NH2:30])=[CH:21][CH:20]=1>C1COCC1.CO>[ClH:10].[OH:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][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:23][CH:24]=1

Participants

5

Reactant 2

HCID 194336464-(5-Aminopentyl)phenolHCID 140329753methyl N-(3,5-diamino-6-chloropyrazine-2-carbonyl)carbamimidothioate;hydroiodide

Product 1

HCID 178479342HCID 178479342, compoundYield 131.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-(3,5-Diamino-6-chloropyrazinoyl-2-methyl-pseudothiourea hydroiodide (0.25 g, 0.65 mmol) was added to a solution of 21 (0.6 g, 3.4 mmol) in THF (50 mL). The reaction mixture was stirred at reflux for 2 h, then the solvent was removed under reduced pressure and the resulting oil was washed with ether (2×50 mL) and treated with ethyl acetate until a yellow powder was formed. The yellow solid was dissolved in methanol (70 mL) and the volume was slowly reduced until precipitation began (approximately 25 mL). The solution was cooled to 0° C. and the precipitate was collected by centrifugation. Diluted HCl (20 mL of a 10% solution) was added and the mixture was vigorously stirred for 20 min, then the precipitate was filtered off, washed with cold water, and dried to give 22 (183 mg, 39%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 1.32 (br s, 2H), 1.55 (m, 4H), 2.45 (m, 2H), 3.29 (m, 2H), 6.68 (d, 2H), 6.97 (d, 2H), 7.46 (s, 1H), 8.00 (br s, 1H), 8.83 (br s, 1H), 8.97 (br s, 1H), 9.46 (d, 2H), 10.55 (s, 1H). APCI MS m/z=392[C17H22ClN7O2+H]+.

Workup

  1. temperatureat reflux for 2 h
  2. customthe solvent was removed under reduced pressure
  3. washthe resulting oil was washed with ether (2×50 mL)
  4. additiontreated with ethyl acetate until a yellow powder
  5. customwas formed
  6. customthe volume was slowly reduced until precipitation
  7. customthe precipitate was collected by centrifugation
  8. additionDiluted HCl (20 mL of a 10% solution) was added
  9. stirringthe mixture was vigorously stirred for 20 min
  10. filtrationthe precipitate was filtered off
  11. washwashed with cold water
  12. customdried

Sources & evidence

ORD record
ord-d5eca2afce334eca85719ee49f9e19cc
Source dataset
uspto-grants-2007_03
Patent number
US07192958B2

Reaction notes

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