Diisopropylethylamine → HCID 178513889, compound

HRID 2420752Notes

Reaction equation

HRID 2420752 reaction equation
C(N(C(C)C)CC)(C)C.Cl.[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH2:25])=[O:24].I.[NH2:27][C:28]1[C:29]([C:36]([NH:38][C:39](=[NH:42])SC)=[O:37])=[N:30][C:31]([Cl:35])=[C:32]([NH2:34])[N:33]=1>C(O)C>[NH2:27][C:28]1[C:29]([C:36]([N:38]=[C:39]([NH2:42])[NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH2:25])=[O:24])=[O:37])=[N:30][C:31]([Cl:35])=[C:32]([NH2:34])[N:33]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 8663423712-Aminododecanoic acid amide hydrochlorideHCID 140329753methyl N-(3,5-diamino-6-chloropyrazine-2-carbonyl)carbamimidothioate;hydroiodide

Product 1

HCID 178513889HCID 178513889, compoundYield 56.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Diisopropylethylamine (0.24 mL, 1.38 mmol) was added to a suspension of 12-amino-dodecanoic acid amide hydrochloride (8) (0.068 g, 0.27 mmol) in absolute ethanol (5 mL). The resulting solution was stirred at 70° C. (oil bath) for 5 min, after which time 1-(3,5-diamino-6-chloropyrazine-2-carbonyl)-2-methylisothiourea hydriodide (115 mg, 0.30 mmol) was added in one portion. The reaction mixture was then stirred at this temperature for 3 hours then cooled to room temperature. After removal of the solvent by rotary evaporation the resulting residue was dissolved in small volume of methanol, and the solution passed through an ion exchange resin column (Dowex 550A OH type). The resin was rinsed with methanol and the methanol solution concentrated in vacuo to a yellow residue. This residue was stirred in a minimal volume of methanol and the resulting solid was collected by suction filtration and washed with a small amount of methanol to give 12-[N′-(3,5-diamino-6-chloropyrazine-2-carbonyl)guanidino]-dodecanoic acid amide 9 (0.065 g, 56%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) 1.23 (m, 14H), 1.49 (m, 4H), 2.01 (t, 2H), 3.11 (m, 2H), 6.65 (m, 4H), 7.21 (br, 1H), 9.06 (br, 1H). m/z (ESI) 427 [C18H31ClN8O2+H]+. mp 192-194° C.

Workup

  1. stirringThe reaction mixture was then stirred at this temperature for 3 hours
  2. temperaturethen cooled to room temperature
  3. customAfter removal of the solvent
  4. customby rotary evaporation the resulting residue
  5. dissolutionwas dissolved in small volume of methanol
  6. washThe resin was rinsed with methanol
  7. concentrationthe methanol solution concentrated in vacuo to a yellow residue
  8. stirringThis residue was stirred in a minimal volume of methanol
  9. filtrationthe resulting solid was collected by suction filtration
  10. washwashed with a small amount of methanol

Sources & evidence

ORD record
ord-ad8776510ca24aebb56d112b08712315
Source dataset
uspto-grants-2011_06
Patent number
US07956059B2

Reaction notes

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