(4-(4-Aminobutyl)phenyl)methanol → HCID 178479336, compound

HRID 217918Notes

Reaction equation

HRID 217918 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][CH2:19][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>[ClH:10].[OH:18][CH2:19][C:20]1[CH:25]=[CH:24][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:22][CH:21]=1

Participants

4

Reactant 2

HCID 11550093(4-(4-Aminobutyl)phenyl)methanolHCID 140329753methyl N-(3,5-diamino-6-chloropyrazine-2-carbonyl)carbamimidothioate;hydroiodide

Product 1

HCID 178479336HCID 178479336, compoundYield 194%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3,5-Diamino-6-chloropyrazinoyl-2-methyl-pseudothiourea hydroiodide (0.2 g, 0.52 mmol) was added to an anhydrous THF suspension (20 mL) of 67 (0.37 g, 2.06 mmol). The reaction mixture was stirred at reflux for 3 h then the solvent was evaporated. The residue was washed with ethyl acetate (3×15 mL), dried and treated with 3% HCl (15 mL). The yellow solid that formed was filtered, washed with water (2×10 mL) and dried to provide 68 (216 mg, 98%). 1H NMR (300 MHz, DMSO-d6) δ 1.57 (br s, 4H), 2.62 (m, 2H), 3.35 (m, 2H), 3.73 (br s, 4H), 4.45 (s, 2H), 7.12 (d, 2H), 7.24 (d, 2H), 8.85 (br s, 1H), 9.98 (br s, 1H), 9.32 (br s, 1H), 10.55 (s, 1H). APCI MS m/z 392 [C17H22ClN7O3+H]+.

Workup

  1. temperatureat reflux for 3 h
  2. customthe solvent was evaporated
  3. washThe residue was washed with ethyl acetate (3×15 mL)
  4. customdried
  5. additiontreated with 3% HCl (15 mL)
  6. customThe yellow solid that formed
  7. filtrationwas filtered
  8. washwashed with water (2×10 mL)
  9. customdried

Sources & evidence

ORD record
ord-803acd564bdd4c8aaeba5e966501984d
Source dataset
uspto-grants-2012_06
Patent number
US08198286B2

Reaction notes

Loading…