[4-(4-Aminobutyl)phenyl]acetic acid → HCID 178479335, compound

HRID 25117Notes

Reaction equation

HRID 25117 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.[C:18]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][NH2:32])=[CH:24][CH:23]=1)([OH:20])=[O:19]>C1COCC1>[ClH:10].[C:18]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][CH2:31][NH:32][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:23]=1)([OH:20])=[O:19]

Participants

4

Reactant 2

HCID 22397301[4-(4-Aminobutyl)phenyl]acetic acidHCID 140329753methyl N-(3,5-diamino-6-chloropyrazine-2-carbonyl)carbamimidothioate;hydroiodide

Product 1

HCID 178479335HCID 178479335, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-(3,5-Diamino-6-chloropyrazinoyl-2-methyl-pseudothiourea hydroiodide (0.2 g, 0.5 mmol) was added to a solution of 8 (0.7 g, 3.4 mmol) in THF (20 mL). The reaction mixture was stirred at reflux for 6 h, then the solvent was evaporated and the resultant oil was treated with 10% HCl (15 mL). The precipitate was isolated and crystallized twice from ethanol to give 9 (53 mg, 25%) as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 1.59 (br s, 4H), 2.71 (m, 2H), 3.83 (s, 3H), 7.40 (d, 2H), 7.48 (br s, 2H), 7.80 (d, 2H), 8.92 (br s, 2H), 9.00 (br s, 1H), 9.48 (br s, 2H), 10.55 (s, 1H). APCI MS m/z=420 [C18H22ClN7O3+H]+.

Workup

  1. temperatureat reflux for 6 h
  2. customthe solvent was evaporated
  3. additionthe resultant oil was treated with 10% HCl (15 mL)
  4. customThe precipitate was isolated
  5. customcrystallized twice from ethanol

Sources & evidence

ORD record
ord-73d0bfeea4114a3dbf805539e1d9f8e3
Source dataset
uspto-grants-2005_02
Patent number
US06858615B2

Reaction notes

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