Hydrochloric Acid → HCID 86725373, compound

HRID 1503816Notes

Reaction equation

HRID 1503816 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([S:11]([CH3:13])=[O:12])[CH:3]=1.[N:14]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O.O>[CH3:13][S:11]([C:4]1[CH:3]=[C:2]([N:17]2[CH2:16][CH2:15][N:14]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18]2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9])=[O:12]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 70556657HCID 70556657, compound

Product 1

HCID 86725373HCID 86725373, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of the product of Example 14B (45 mg, 0.17 mmol), tert-butyl piperazine-1-carboxylate (38 mg, 0.2 mmol), tetrabutylammonium bromide (6 mg, 0.02 mmol) and potassium carbonate (35 mg, 0.26 mmol) in dry DMSO (5 mL) was heated under nitrogen at 120° C. for 3 hours. The mixture was added to water (20 mL) and aqueous hydrogen chloride solution (20 mL) and washed with ethyl acetate. The aqueous phase was basified with 2.5N sodium hydroxide solution and extracted with ethyl acetate (3×20 mL). The combined organic phase was dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 40/1 dichloromethane/methanol to give the title compound.

Workup

  1. washwashed with ethyl acetate
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel eluting with 40/1 dichloromethane/methanol

Sources & evidence

ORD record
ord-04860c4f9140491cba2304aff332a4b4
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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