Triethylamine → HCID 178453552, compound

HRID 254373Notes

Reaction equation

HRID 254373 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(N(CC)CC)C.[C:25]([O:29][C:30](=[O:48])[NH:31][CH2:32][CH2:33][C:34](=[O:47])[NH:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][CH2:44][CH2:45][NH2:46])=[CH:38][CH:37]=1)([CH3:28])([CH3:27])[CH3:26]>C(O)C>[C:25]([O:29][C:30](=[O:48])[NH:31][CH2:32][CH2:33][C:34](=[O:47])[NH:35][C:36]1[CH:41]=[CH:40][C:39]([CH2:42][CH2:43][CH2:44][CH2:45][NH:46][C:14]([NH2:17])=[N: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])=[CH:38][CH:37]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 58664836{2-[4-(4-Aminobutyl)phenylcarbamoyl]ethyl}carbamic acid tert-butyl esterHCID 140329753methyl N-(3,5-diamino-6-chloropyrazine-2-carbonyl)carbamimidothioate;hydroiodide

Product 1

HCID 178453552HCID 178453552, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

1-(3,5-Diamino-6-chloropyrazine-2-carbonyl)-2-methylisothiourea hydriodide (0.32 g, 0.82 mmol) and triethylamine (0.42 mL) were added to a solution of {2-[4-(4-amino-butyl)phenylcarbamoyl]ethyl}carbamic acid tert-butyl ester 340 (0.25 g, 0.74 mmol) in ethanol (6 mL). The reaction mixture was stirred at 65° C. for 3 hours, and cooled to room temperature. The solvent was evaporated in vacuo. The residue was purified by flash chromatography (silica gel, 10:1:0.1 to 5:1:0.1, v/v chloroform/methanol/concentrated ammonium hydroxide). The product was washed with water (2×25 mL) and dried in a vacuum oven overnight to provide 350 (0.32 g, 78%) as a yellow solid. 1H NMR (300 MHz, CD3OD) δ 1.44 (s, 9H), 1.69 (m, 4H), 2.57 (t, 2H), 2.66 (t, 2H), 3.27 (t, 2H), 3.40 (m, 2H), 7.15 (d, 2H), 7.47 (d, 2H).

Workup

  1. temperaturecooled to room temperature
  2. customThe solvent was evaporated in vacuo
  3. customThe residue was purified by flash chromatography (silica gel, 10:1:0.1 to 5:1:0.1, v/v chloroform/methanol/concentrated ammonium hydroxide)
  4. washThe product was washed with water (2×25 mL)
  5. customdried in a vacuum oven overnight

Sources & evidence

ORD record
ord-8bc0c93068cb437db6fcd425d436ab71
Source dataset
uspto-grants-2011_01
Patent number
US07875619B2

Reaction notes

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