3-Amino-1-propanol → HCID 59333306, compound

HRID 1893473Notes

Reaction equation

HRID 1893473 reaction equation
[Br:1][C:2]1[N:6]2[C:7]3[C:12]([N:13]=[C:14](Cl)[C:5]2=[N:4][CH:3]=1)=[CH:11][C:10]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:9][CH:8]=3.[NH2:21][CH2:22][CH2:23][CH2:24][OH:25]>O1CCOCC1.C(OCC)(=O)C>[Br:1][C:2]1[N:6]2[C:7]3[C:12]([N:13]=[C:14]([NH:21][CH2:22][CH2:23][CH2:24][OH:25])[C:5]2=[N:4][CH:3]=1)=[CH:11][C:10]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:9][CH:8]=3

Participants

5

Reactant 2

HCID 90863-Amino-1-propanolHCID 59333304HCID 59333304, compound

Product 1

HCID 59333306HCID 59333306, compoundYield 87.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of 1-bromo-4-chloro-7-trifluoromethoxy-imidazo[1,2-a]quinoxaline (6.5 g, 17.7 mmol, 1 eq) in dioxane (87 mL) is added 3-aminopropan-1-ol (3.4 mL; 44.3 mmol; 2.5 eq). The resulting solution is then heated at reflux for 16 hours until completion of the reaction. The mixture is diluted with ethyl acetate (100 mL) and washed with a 1M aqueous solution of sodium hydroxide (50 mL). The organic layer is separated, dried over sodium sulphate and concentrated in vacuo to afford a beige solid. This powder is washed with diethyl ether to afford after filtration the title compound (6.3 g; 15.5 mmol; 87%) with a 99% HPLC purity.

Workup

  1. temperatureThe resulting solution is then heated
  2. temperatureat reflux for 16 hours until completion of the reaction
  3. washwashed with a 1M aqueous solution of sodium hydroxide (50 mL)
  4. customThe organic layer is separated
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. customto afford a beige solid
  8. washThis powder is washed with diethyl ether
  9. customto afford

Sources & evidence

ORD record
ord-63ee1e835b3545a2bc8062d6cbf74d82
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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