Potassium tert-butoxide → HCID 86677567, compound

HRID 2401110Notes

Reaction equation

HRID 2401110 reaction equation
C([O:3][C:4]([C:6]1([CH2:19][CH2:20][NH:21][C:22]2[CH:27]=[N:26][C:25]([Br:28])=[CH:24][N:23]=2)[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=O)C.CC(C)([O-])C.[K+]>C1COCC1.C(OCC)(=O)C>[C:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][C:6]2([C:4](=[O:3])[N:21]([C:22]3[CH:27]=[N:26][C:25]([Br:28])=[CH:24][N:23]=3)[CH2:20][CH2:19]2)[CH2:7][CH2:8]1)=[O:13])([CH3:17])([CH3:16])[CH3:18]

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxide2×HCID 866775664-[2-(5-Bromo-pyrazin-2-ylamino)-ethyl]-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

Product 1

HCID 86677567HCID 86677567, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[2-(5-bromo-pyrazin-2-ylamino)-ethyl]-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (0.825 g, 1.81 mmols) in THF (10 mL) was added a 1 M solution of potassium t-butoxide in THF (2.0 mL), and allowed to stir at room temperature. After 1 hour LCMS was taken and reaction was not complete. After 5 hours, an additional 1 mL of potassium t-butoxide was added. The reaction mixture was allowed to stir for 16 hours. The three reaction mixtures were diluted with ethyl acetate (20 mL), quenched with water (5 mL). The aqueous layer was extracted with EtOAc (2×10 mL). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated under vacuum to afford crude product. Purification over silica gel eluting with methanol in dichloromethane (0-10%) afforded 0.186 g (25%) of the title compound.

Workup

  1. customreaction
  2. waitAfter 5 hours
  3. stirringto stir for 16 hours
  4. customThe three reaction mixtures
  5. customquenched with water (5 mL)
  6. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated under vacuum
  10. customto afford crude product
  11. customPurification over silica gel eluting with methanol in dichloromethane (0-10%)

Sources & evidence

ORD record
ord-eff813216728484da0543360c681b540
Source dataset
uspto-grants-2014_08
Patent number
US08796278B2

Reaction notes

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