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

HRID 1911137Notes

Reaction equation

HRID 1911137 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-c1e7220a237745889ee38b69f716a4b6
Source dataset
uspto-grants-2013_12
Patent number
US08604017B2

Reaction notes

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