1,4-Dioxane → HCID 178520834, compound

HRID 1893470Notes

Reaction equation

HRID 1893470 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[N:15]3[C:16]4[C:21]([N:22]=[C:23]([NH:24][CH2:25][CH2:26][CH2:27][OH:28])[C:14]3=[N:13][CH:12]=2)=[CH:20][C:19]([C:29]([F:32])([F:31])[F:30])=[CH:18][CH:17]=4)[NH:8][N:7]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O1CCOCC1>C1COCC1>[OH:3][CH2:4][C:6]1[CH:10]=[C:9]([C:11]2[N:15]3[C:16]4[C:21]([N:22]=[C:23]([NH:24][CH2:25][CH2:26][CH2:27][OH:28])[C:14]3=[N:13][CH:12]=2)=[CH:20][C:19]([C:29]([F:30])([F:32])[F:31])=[CH:18][CH:17]=4)[NH:8][N:7]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 21226445Aluminium lithium hydrideHCID 178468649HCID 178468649, compound

Product 1

HCID 178520834HCID 178520834, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-[4-(3-Hydroxy-propylamino)-7-trifluoromethyl-imidazo[1,2-a]quinoxalin-1-yl]-1H-pyrazole-3-carboxylic acid ethyl ester (0.08 mmol; 36 mg), in THF (0.2 mL) under argon cooled to 0° C., was added LAH (0.24 mmol; 10 mg). The reaction was slowly warmed up to room temperature over 4 hr, then to 45° C. overnight. After addition of dioxane (1 mL), the mixture was heated to 75° C. for 24 hr. After quenching with Rochelle's salt, the mixture was extracted with ethyle acetate. The organic phase was dried, concentrated. The residue was purified by preparative TLC (dichloromethane/methanol) to yield the title compound as a white solid (7 mg; 0.02 mmol; 21%).

Workup

  1. customto 45° C.
  2. customovernight
  3. temperaturethe mixture was heated to 75° C. for 24 hr
  4. customAfter quenching with Rochelle's salt
  5. extractionthe mixture was extracted with ethyle acetate
  6. customThe organic phase was dried
  7. concentrationconcentrated
  8. customThe residue was purified by preparative TLC (dichloromethane/methanol)

Sources & evidence

ORD record
ord-cbe2b925a5284d3692fc358892bf8d4c
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

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