Potassium Carbonate → 1-Acetyl-6-bromo-2-({3-[piperazin-yl]azetidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinoline

HRID 2365305Notes

Reaction equation

HRID 2365305 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([Br:14])=[CH:11][CH:12]=2)[CH2:7][CH2:6][CH:5]1[C:15]([N:17]1[CH2:20][CH:19]([N:21]2[CH2:26][CH2:25][N:24](C(=O)C(F)(F)F)[CH2:23][CH2:22]2)[CH2:18]1)=[O:16])(=[O:3])[CH3:2].C([O-])([O-])=O.[K+].[K+]>CO>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([Br:14])=[CH:11][CH:12]=2)[CH2:7][CH2:6][CH:5]1[C:15]([N:17]1[CH2:20][CH:19]([N:21]2[CH2:22][CH2:23][NH:24][CH2:25][CH2:26]2)[CH2:18]1)=[O:16])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 596259251-Acetyl-6-bromo-2-({3-[4-(trifluoroacetyl)piperazin-1-yl]azetidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinoline

Product 1

HCID 596259321-Acetyl-6-bromo-2-({3-[piperazin-yl]azetidin-1-yl}carbonyl)-1,2,3,4-tetrahydroquinolineYield 74.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound 25d (261 mg, 0.505 mmol) in MeOH (3 mL) was added K2CO3 (140 mg, 1.01 mmol). The reaction mixture was stirred at room temperature for 30 min. The resultant mixture was filtered, the filtrate concentrated under reduced pressure, and the resultant residue partitioned between CH2Cl2 and H2O. The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure to give compound 25e (158 mg). LC/MS m/z (M+H+) 421.0, (M+2H+) 423.0.

Workup

  1. filtrationThe resultant mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customthe resultant residue partitioned between CH2Cl2 and H2O
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0599361d0759409fab100adb36b6aa32
Source dataset
uspto-grants-2014_04
Patent number
US08697684B2

Reaction notes

Loading…