Methanol → HCID 54591668, compound

HRID 509254Notes

Reaction equation

HRID 509254 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.Br[CH2:27][CH2:28][OH:29].C(=O)([O-])[O-].[K+].[K+].CO>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](=[O:25])[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N:19]3[CH2:20][CH2:21][N:22]([CH2:27][CH2:28][OH:29])[CH2:23][CH2:24]3)[N:14]=1)[CH2:8]2

Participants

6

Reactant 4

HCID 887MethanolHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 54591596HCID 54591596, compound

Product 1

HCID 54591668HCID 54591668, compoundYield 96.2%

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), 2-bromoethanol (19 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 18 hours. The resulting reaction liquid was concentrated under reduced pressure, and then the residue thus obtained was subjected to MPLC (10% MeOH/MC), to obtain 37 mg of colorless oil (96%). MS (ESI): 385 [M+H]+

Workup

  1. customThe resulting reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. customthe residue thus obtained

Sources & evidence

ORD record
ord-3a364abe512f40cbb08cd1fa74e3b391
Source dataset
uspto-grants-2015_08
Patent number
US09096571B2

Reaction notes

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