Ethyl Acetate → HCID 71231645, compound

HRID 2175369Notes

Reaction equation

HRID 2175369 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([C:22]3[CH:23]=[C:24]4[NH:33][C:32](=[O:34])[C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[N:25]4[CH:35]=3)=O)[CH2:16][CH2:15]2)=[CH:10][CH:9]=1.C(OCC)(=O)C.O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>O1CCCC1.O>[F:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]2[CH2:15][CH2:16][N:17]([CH2:20][C:22]3[CH:23]=[C:24]4[NH:33][C:32](=[O:34])[C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[N:25]4[CH:35]=3)[CH2:18][CH2:19]2)=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 2724148Sodium potassium tartrate tetrahydrateHCID 21226445Aluminium lithium hydrideHCID 71231658HCID 71231658, compound2×

Product 1

HCID 71231645HCID 71231645, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under cooling on ice, lithium aluminum hydride (657 mg, 17.3 mmol) was added to a solution of 2-[4-(4-fluorophenyl)piperazine-1-carbonyl]pyrrolo[1,2-a]quinazolin-5(4H)-one (the above Compound 1-1, 3.38 g, 8.66 mmol) in anhydrous tetrahydrofuran (75 mL). This reaction solution was stirred at room temperature for 2 hours. A small amount of ethyl acetate was added dropwise to the reaction solution, and then a saturated aqueous solution of sodium potassium tartrate tetrahydrate (100 mL), and water (100 mL) were added sequentially. The mixture was extracted twice with chloroform (100 mL). The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was collected by filtration with ethanol, to obtain the title compound (2.85 g, yield: 87%) as a pale yellow powder.

Workup

  1. extractionThe mixture was extracted twice with chloroform (100 mL)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. filtrationThe obtained residue was collected by filtration with ethanol

Sources & evidence

ORD record
ord-3e3c3f340f594cc5927cec1323100e0c
Source dataset
uspto-grants-2015_06
Patent number
US09062061B2

Reaction notes

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