3,3-Dimethylbutanoyl chloride → 6-[4-(3,3-dimethyl-butyryl)-piperazin-1-yl]-N-(3-iodo-4-methyl-phenyl)-nicotinamide

HRID 2190669Notes

Reaction equation

HRID 2190669 reaction equation
[CH3:1][C:2]([CH3:8])([CH3:7])[CH2:3][C:4](Cl)=[O:5].[I:9][C:10]1[CH:11]=[C:12]([NH:17][C:18](=[O:31])[C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[N:21][CH:20]=2)[CH:13]=[CH:14][C:15]=1[CH3:16]>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][C:2]([CH3:8])([CH3:7])[CH2:3][C:4]([N:28]1[CH2:29][CH2:30][N:25]([C:22]2[CH:23]=[CH:24][C:19]([C:18]([NH:17][C:12]3[CH:13]=[CH:14][C:15]([CH3:16])=[C:10]([I:9])[CH:11]=3)=[O:31])=[CH:20][N:21]=2)[CH2:26][CH2:27]1)=[O:5]

Participants

5

Reactant 2

HCID 815143,3-Dimethylbutanoyl chlorideHCID 59318071N-(3-Iodo-4-methyl-phenyl)-6-piperazin-1-yl-nicotinamide

Product 1

HCID 593181756-[4-(3,3-dimethyl-butyryl)-piperazin-1-yl]-N-(3-iodo-4-methyl-phenyl)-nicotinamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-[4-(3,3-Dimethyl-butyryl)-piperazin-1-yl]-N-(3-iodo-4-methyl-phenyl)-nicotinamide was synthesized by the addition 3,3-dimethyl-butyryl chloride (0.055 mmol) to N-(3-iodo-4-methyl-phenyl)-6-piperazin-1-yl-nicotinamide (0.05 mmol) partially dissolved in DCM followed by the addition of TEA and stirred at room temperature over night. The reaction was diluted with ethyl acetate washed with water and brine, dried over sodium sulfate, concentrated and the residue was trirturated with ether and hexanes to afford the product, 6-[4-(3,3-dimethyl-butyryl)-piperazin-1-yl]-N-(3-iodo-4-methyl-phenyl)-nicotinamide. LCMS calcd for C23H29IN4O2 (m/e) 520, obsd 521 (M+H).

Workup

  1. additionfollowed by the addition of TEA
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-324f13d342824672a5063f5167af2e6b
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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