Isobutyl chloroformate → HCID 66883005, compound

HRID 1784040Notes

Reaction equation

HRID 1784040 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][C:9](=[CH2:11])[CH2:8][C@@H:7]1[C:12]([OH:14])=O)=[O:5])[CH3:2].ClC(OCC(C)C)=O.[NH2:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]2=[O:36])=[CH:26][C:25]=1[F:37]>C1COCC1.CN1CCOCC1.CN(C=O)C>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:10][C:9](=[CH2:11])[CH2:8][C@@H:7]1[C:12](=[O:14])[NH:23][C:24]1[CH:29]=[CH:28][C:27]([N:30]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]2=[O:36])=[CH:26][C:25]=1[F:37])=[O:5])[CH3:2]

Participants

7

Reactant 3

HCID 62365Isobutyl chloroformateHCID 221815481-(4-Amino-3-fluorophenyl)pyridin-2-oneHCID 57590164HCID 57590164, compound

Product 1

HCID 66883005HCID 66883005, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 79724-MethylmorpholineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.0 g of 41b in 10 ml of THF and 0.61 ml of N-methylmorpholine was added at −12° C. 0.72 ml of isobutyl chloroformate and stirring was continued at −15° C. for 30 min and at 20° C. for 1 h. The suspension obtained was added to a hot (60° C.) solution of 1.13 g of 1-(4-amino-3-fluoro-phenyl)-1H-pyridin-2-one (prepared according to C. F. Bigge et al., patent application WO 2003045912) in 8 ml of DMF and stirring was continued at 60° C. for 1 h. The reaction mixture was evaporated and the residue partitioned between 1 N HCl and AcOEt, the organic layer was washed with HCl and brine, dried and evaporated. The residue was chromatographed on silica using heptane/AcOEt (1:2) to give 1.28 g of the title compound 54a. MS: 385.0 (M+H)+.

Workup

  1. customThe suspension obtained
  2. waitwas continued at 60° C. for 1 h
  3. customThe reaction mixture was evaporated
  4. customthe residue partitioned between 1 N HCl and AcOEt
  5. washthe organic layer was washed with HCl and brine
  6. customdried
  7. customevaporated
  8. customThe residue was chromatographed on silica

Sources & evidence

ORD record
ord-f785e51d06b84c14b68035a34ef9de19
Source dataset
uspto-grants-2009_03
Patent number
US07501413B2

Reaction notes

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