4-(3,4-Dihydroxyphenyl)butyl amine hydrobromide → HCID 178479341, compound

HRID 1294544Notes

Reaction equation

HRID 1294544 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:21]=[C:22]([CH2:27][CH2:28][CH2:29][CH2:30][NH2:31])[CH:23]=[CH:24][C:25]=1[OH:26]>C1COCC1.C(N(CC)CC)C>[ClH:10].[OH:19][C:20]1[CH:21]=[C:22]([CH2:27][CH2:28][CH2:29][CH2:30][NH:31][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][C:25]=1[OH:26]

Participants

5

Reactant 2

HCID 116446304-(3,4-Dihydroxyphenyl)butyl amine hydrobromideHCID 140329753methyl N-(3,5-diamino-6-chloropyrazine-2-carbonyl)carbamimidothioate;hydroiodide

Product 1

HCID 178479341HCID 178479341, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

1-(3,5-Diamino-6-chloropyrazinoyl-2-methyl-pseudothiourea hydroiodide (0.2 g, 0.51 mmol) was added to a suspension of 27 in a mixture of THF (35 mL) and triethylamine (3 mL). The reaction mixture was stirred at reflux for 3 h, then the supernatant was separated and the solvent was removed under reduced pressure. The brown residue was washed with ether (2×30 mL) followed by addition of 10% HCl (5 mL). The solid material was collected, dissolved in methanol and precipitated by addition of ethyl acetate. The precipitate was washed with 10% HCl and dried to give compound 28 (131 mg, 51%) as a beige solid. 1H NMR (300 MHz, DMSO-d6) δ 1.52 (br s, 4H), 2.42 (m, 2H), 3.31 (m, 2H), 6.43 (m, 1H), 6.61 (m, 2H), 7.42 (br s, 2H), 7.90 (br s, 1H), 8.82 (br s, 1H), 8.98 (br s, 1H), 9.25 (s, 1H) 10.52 (s, 1H). APCI MS m/z=394 [C16H20ClN7O3+H]+.

Workup

  1. temperatureat reflux for 3 h
  2. customthe supernatant was separated
  3. customthe solvent was removed under reduced pressure
  4. washThe brown residue was washed with ether (2×30 mL)
  5. additionfollowed by addition of 10% HCl (5 mL)
  6. customThe solid material was collected
  7. dissolutiondissolved in methanol
  8. customprecipitated by addition of ethyl acetate
  9. washThe precipitate was washed with 10% HCl
  10. customdried

Sources & evidence

ORD record
ord-258b737f5012445db507a40bc60f4fd4
Source dataset
uspto-grants-2007_07
Patent number
US07241766B2

Reaction notes

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