Potassium Carbonate → HCID 54591669, compound

HRID 509255Notes

Reaction equation

HRID 509255 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12](=[O:25])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[N:14]=1)[CH2:8]2.[CH3:26][O:27][C:28](=[O:32])[CH2:29][CH2:30]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12]([C:13]1[N:14]=[C:15]([N:19]3[CH2:20][CH2:21][N:22]([CH2:30][CH2:29][C:28]([O:27][CH3:26])=[O:32])[CH2:23][CH2:24]3)[CH:16]=[CH:17][CH:18]=1)=[O:25])[CH2:8]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76934Methyl 3-bromopropanoateHCID 54591596HCID 54591596, compound

Product 1

HCID 54591669HCID 54591669, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

After N-(adamantan-2-yl)-6-(piperazin-1-yl)picolinamide (34 mg, 0.100 mmol) was dissolved in DMF (2 ml), 3-bromopropanoic acid methyl ester (25 mg, 0.150 mmol) and potassium carbonate (41 mg, 0.300 mmol) were added thereto, and then the resulting mixture was stirred at 100° C. under nitrogen stream for 24 hours. The resulting reaction liquid was filtered and concentrated under reduced pressure, and then the residue thus obtained was subjected to MPLC (60% EtOAc/Hexanes), to obtain 41 mg of white solid (96%). MS (ESI): 427 [M+H]+

Workup

  1. customThe resulting reaction liquid
  2. filtrationwas filtered
  3. concentrationconcentrated under reduced pressure
  4. customthe residue thus obtained

Sources & evidence

ORD record
ord-854993c3436c4d9db524b488b8733bb9
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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