Triethylamine → HCID 178508788, compound

HRID 2365479Notes

Reaction equation

HRID 2365479 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C@H:11]2[CH2:15][NH:14]/[C:13](=[N:16]\[C:17]([C:19]3[C:24]([NH2:25])=[N:23][C:22]([NH2:26])=[C:21]([Cl:27])[N:20]=3)=[O:18])/[NH:12]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:35]1[O:37][C@H:36]1[CH2:38][OH:39]>C(O)C.CO>[OH:37][C@@H:36]([CH2:38][OH:39])[CH2:35][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C@H:11]2[CH2:15][NH:14]/[C:13](=[N:16]/[C:17]([C:19]3[C:24]([NH2:25])=[N:23][C:22]([NH2:26])=[C:21]([Cl:27])[N:20]=3)=[O:18])/[NH:12]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 6973630(-)-GlycidolHCID 178508785HCID 178508785, compound

Product 1

HCID 178508788HCID 178508788, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of 3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid [(S)-4-[3-(4-hydroxy-phenyl)-propyl]-imidazolidin-(2E)-ylidene]-amide (Example 18) (37.5 mg, 0.09 mmol) in Ethanol (2 ml) is added triethylamine (63 l, 0.45 mmol) and (S)-glycidol (6.07 l, 0.09 mmol). The resulting mixture is heated at reflux for 18 hours and then allowed to cool to room temperature. The reaction mixture is diluted with MeOH (1 ml) and purified on a Waters 3000 prep HPLC system, (Microsorb C18, Water (0.1% TFA): MeCN) to afford the title compound; [M+H]+ 464.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for 18 hours
  3. custompurified on a Waters 3000 prep HPLC system, (Microsorb C18, Water (0.1% TFA): MeCN)

Sources & evidence

ORD record
ord-8e53af9992b14e05a0ae95089d89160d
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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