Phenethylamine → HCID 68677389, compound

HRID 2233027Notes

Reaction equation

HRID 2233027 reaction equation
[C:1]([N:5]1[C:26](=[O:27])[N:8]2[CH:9]=[C:10]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([OH:22])=O)[N:11]=[C:12]([NH:13][CH:14]([CH3:16])[CH3:15])[C:7]2=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH2:28]([NH2:36])[CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C(N(CC)CC)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>CCOC(C)=O>[C:1]([N:5]1[C:26](=[O:27])[N:8]2[CH:9]=[C:10]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=3)[C:20]([NH:36][CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:22])[N:11]=[C:12]([NH:13][CH:14]([CH3:16])[CH3:15])[C:7]2=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 111923Propylphosphonic anhydrideHCID 68675444HCID 68675444, compound

Product 1

HCID 68677389HCID 68677389, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 50 mg of the product of Step A, 33 mg of phenethylamine, 68 mg of triethylamine and 258 mg of 1-propanephosphonic acid cyclic anhydride in EtOAc (3.0 mL) was warmed to 80° C. The organic layer was washed with sat. sodium chloride solution, dried over sodium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography to afford 3-(2-tert-butyl-8-isopropylamino-3-oxo-2,3-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-6-yl)-N-phenethyl-benzamide as a white solid. MS (M+H+)=473.4.

Workup

  1. washThe organic layer was washed with sat. sodium chloride solution
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-14e94f259a9e4a25a2f0f98d28596f4d
Source dataset
uspto-grants-2010_05
Patent number
US07709473B2

Reaction notes

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