Pivaloyl chloride → HCID 59743959, compound

HRID 602101Notes

Reaction equation

HRID 602101 reaction equation
[NH:1]1[CH2:4][CH:3]([NH:5][C:6](=[O:20])[C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)=[N:9][CH:8]=2)[CH2:2]1.CCN(C(C)C)C(C)C.[C:30](Cl)(=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32]>CN(C=O)C.C(OCC)(=O)C.O>[CH3:32][C:31]([CH3:34])([CH3:33])[C:30]([N:1]1[CH2:4][CH:3]([NH:5][C:6](=[O:20])[C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[CH:14]=3)=[N:9][CH:8]=2)[CH2:2]1)=[O:35]

Participants

7

Reactant 3

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 59743772HCID 59743772, compound

Product 1

HCID 59743959HCID 59743959, compoundYield 117.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-azetidin-3-yl-6-(3-fluorophenyl)nicotinamide (50 mg, 0.12 mmol) in DMF (1 mL) was added DIPEA (0.06 mL, 0.32 mmol) and pivaloyl chloride (29.4 mg, 0.24 mmol). The reaction mixture was stirred at room temperature overnight and then diluted with ethyl acetate and water. The layers were separated and the organic layer washed with brine, dried (MgSO4) and the solvent removed to give a solid, which was purified by chromatography (silica, 80% etoac:hex) to give the desired product, N-[1-(2,2-dimethylpropanoyl)azetidin-3-yl]-6-(3-fluorophenyl)nicotinamide (50 mg, 86%). HRMS (M+H)=356.1856 observed, 356.1774 expected.

Workup

  1. customThe layers were separated
  2. washthe organic layer washed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed
  5. customto give a solid, which
  6. customwas purified by chromatography (silica, 80% etoac:hex)

Sources & evidence

ORD record
ord-51de906279f1447a88e7a90a6e10259b
Source dataset
uspto-grants-2011_03
Patent number
US07902373B2

Reaction notes

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