Hydrochloric Acid → HCID 66912254, compound

HRID 1990890Notes

Reaction equation

HRID 1990890 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][C:5]=2[N:6]=1.C(N(C(C)C)C(C)C)C.[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([NH2:35])[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].Cl>C(#N)C>[C:22]([O:26][C:27]([N:29]1[CH2:34][CH2:33][CH:32]([NH:35][C:2]2[O:3][C:4]3[CH:10]=[CH:9][C:8]([C:11]#[N:12])=[CH:7][C:5]=3[N:6]=2)[CH2:31][CH2:30]1)=[O:28])([CH3:25])([CH3:23])[CH3:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 106311802-Chloro-5-benzoxazolecarbonitrile

Product 1

HCID 66912254HCID 66912254, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-chloro-benzooxazole-5-carbonitrile (5.0 g, 28.0 mmol, 1.0 equiv; prepared as described in A. Batista-Parra, S. Venkitachalam, W. D. Wilson, D. W. Boykin Heterocycles 2003, 60, 1367-1376) in acetonitrile (65 mL) was added N-ethyl diisopropylamine (36.0 mL, 27.1 g, 210.0 mmol, 7.5 equiv) and 4-amino-piperidine-1-carboxylic acid tert-butyl ester (5.61 g, 28.0 mmol, 1.0 equiv). The reaction mixture was stirred at rt for 18 h under Ar, poured on crashed ice and the pH adjusted by addition of a solution of 37% HCl to pH 3.0. The reaction mixture was extracted with ethyl acetate (3×100 mL), the combined organic phases washed with water and dried over MgSO4. The organic solvent was evaporated under reduced pressure and the crude reaction product purified with column chromatography on silica eluting with a gradient of dichloromethane/methanol (100:0→95:5) to give 7.31 g (76%) of the title compound. MS (ESI): 343.0 [M+H]+.

Workup

  1. customprepared
  2. additionpoured
  3. extractionThe reaction mixture was extracted with ethyl acetate (3×100 mL)
  4. washthe combined organic phases washed with water
  5. dry with materialdried over MgSO4
  6. customThe organic solvent was evaporated under reduced pressure
  7. customthe crude reaction product
  8. custompurified with column chromatography on silica eluting with a gradient of dichloromethane/methanol (100:0→95:5)

Sources & evidence

ORD record
ord-8b42654d0ad24506ab8d1b19230d295c
Source dataset
uspto-grants-2010_01
Patent number
US07645753B2

Reaction notes

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