Potassium Carbonate → HCID 76672297, compound

HRID 2363020Notes

Reaction equation

HRID 2363020 reaction equation
[O:1]=[C:2]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][N:3]1[CH2:18][C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].[CH3:32][O:33][N:34]=[C:35]([C:40]1[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=1)[CH2:36][CH2:37][CH2:38]I.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[F:46][C:43]1[CH:42]=[CH:41][C:40]([C:35](=[N:34][O:33][CH3:32])[CH2:36][CH2:37][CH2:38][N:9]2[CH2:10][CH2:11][C:6]3([N:5]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:4][N:3]([CH2:18][C:19]4[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=4)[C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[C:2]3=[O:1])[CH2:7][CH2:8]2)=[CH:45][CH:44]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 58046667Tert-butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoateHCID 76672298HCID 76672298, compound

Product 1

HCID 76672297HCID 76672297, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 3-((4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decan-3-yl)methyl)benzoate (0.25 g, 0.593 mmol), 1-(4-fluorophenyl)-4-iodobutan-1-one O-methyl oxime (0.19 g, 0.593 mmol), and potassium carbonate (0.12 g, 0.890 mmol) in N,N-dimethylformamide (8 mL) were stirred at 65° C. for 2 hours. The reaction was diluted with ethyl acetate, washed with water and brine, dried (MgSO4), and evaporated. The residue was purified by PTLC (5% methanol/dichloromethane) to give product as an oil (0.28 g, 78%); MS for C36H43FN4O4 m/z 615 (M+H)+.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by PTLC (5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-f2a956ca682d4d19b069943a27ed2e14
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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