Diisopropylethylamine → 4-(6-Methoxy-pyridine-2-carbonyl)-3,3-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 334079Notes

Reaction equation

HRID 334079 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=1.ClC(N(C)C)=C(C)C.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][NH:30][C:29]([CH3:34])([CH3:33])[CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].CCN(C(C)C)C(C)C>C1COCC1.C([O-])(O)=O.[Na+]>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][N:30]([C:9]([C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:8]=2)=[O:11])[C:29]([CH3:34])([CH3:33])[CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5708916-Methoxypicolinic acidHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 227103871-Boc-3,3-dimethylpiperazine

Product 1

HCID 866883014-(6-Methoxy-pyridine-2-carbonyl)-3,3-dimethyl-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 410 mg (2.28 mmol) 6-methoxy-2-pyridinecarboxylic acid and 400 μL (3.02 mmol) 1-chloro-N,N,2-trimethylpropenylamine in 10 mL THF was stirred at RT. After 1.5 h, 600 mg (2.66 mmol) 3,3-dimethyl-piperazine-1-carboxylic acid tert-butyl ester and 1.00 mL (5.81 mmol) DIPEA was added and the reaction mixture was stirred at RT for 30 min. The reaction mixture was diluted with saturated NaHCO3 solution and extracted with EtOAc. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (PE/EtOAc=1/1).

Workup

  1. stirringthe reaction mixture was stirred at RT for 30 min
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (PE/EtOAc=1/1)

Sources & evidence

ORD record
ord-260674243acf4dd5bc9d09582171236f
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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