Ethyl Acetate → HCID 178434265, compound

HRID 490107Notes

Reaction equation

HRID 490107 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:12]=[N:13][CH:14]=[C:15]([N:17]4[CH2:22][CH2:21][NH:20][C@@H:19]([CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:18]4)[N:16]=3)[CH:9]=2)[NH:4][N:3]=1.C(=O)(O)[O-].[Na+].Br[CH2:36][CH2:37][OH:38].C(OCC)(=O)C>C(#N)C>[CH2:23]([C@@H:19]1[N:20]([CH2:36][CH2:37][OH:38])[CH2:21][CH2:22][N:17]([C:15]2[N:16]=[C:11]([C:8]3[CH:9]=[C:10]4[C:5](=[CH:6][CH:7]=3)[NH:4][N:3]=[C:2]4[CH3:1])[N:12]=[N:13][CH:14]=2)[CH2:18]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 108982-BromoethanolHCID 516892Sodium BicarbonateHCID 178434266HCID 178434266, compound

Product 1

HCID 178434265HCID 178434265, compoundYield 7.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-[(S)-3-benzylpiperazin-1-yl]-3-(3-methylindazol-5-yl)-[1,2,4]triazine 12 (28.5 mg, 0.074 mmol.) in acetonitrile (2 mL) was added sodium bicarbonate (6.2 mg, 0.074 mmol.) and 2-bromoethanol (9.2 mg, 0.11 mmol.). The reaction mixture was heated under gentle reflux overnight. Ethyl acetate (50 mL) was added. The organic layer was washed with water and brine. The organic layer was dried over sodium sulfate. The organic solvent was evaporated under reduced pressure. The crude product was purified by RP-HPLC to yield the desired 5-[(S)-3-benzyl-4-hydroxyethyl-piperazin-1-yl]-3-(3-methylindazol-5-yl)-[1,2,4]triazine 60 (2.3 mg, 0.0054 mmol.).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder gentle reflux overnight
  3. washThe organic layer was washed with water and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customThe organic solvent was evaporated under reduced pressure
  6. customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record
ord-fb76d5a42b144ff3aa36cbd3e12496a3
Source dataset
uspto-grants-2009_05
Patent number
US07528132B2

Reaction notes

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