Potassium Carbonate → HCID 178483669, compound

HRID 526210Notes

Reaction equation

HRID 526210 reaction equation
C([O:4][CH2:5][C:6]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[NH:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([CH2:25][N:26]([CH3:28])[CH3:27])[CH2:21][CH2:20]1)=[N:15][C:14]([Cl:29])=[CH:13][CH:12]=2)=[O:7])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:29][C:14]1[N:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][C:8]([C:6](=[O:7])[CH2:5][OH:4])=[C:17]2[NH:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([CH2:25][N:26]([CH3:28])[CH3:27])[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 178476434HCID 178476434, compound

Product 1

HCID 178483669HCID 178483669, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-(6-chloro-4-{trans-4-[(dimethylamino)methyl]cyclohexylamino}-1,5-naphthyridin-3-yl)-2-oxoethyl acetate (90 mg, 0.22 mmol) in methanol was added freshly ground potassium carbonate (90 mg, 0.65 mmol) and the reaction mixture was stirred at room temperature for 30 minutes. The reaction mixture was diluted with satd. aq. sodium bicarbonate and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated. The residue was purified by column chromatography (silica, dichloromethane/methanol) to afford the desired product (18 mg, 22%) as a yellow solid. ESI MS m/z 377 [M+H]+.

Workup

  1. additionThe reaction mixture was diluted with satd
  2. extractionaq. sodium bicarbonate and extracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by column chromatography (silica, dichloromethane/methanol)

Sources & evidence

ORD record
ord-26123b82890648a48be893425ababa3d
Source dataset
uspto-grants-2016_05
Patent number
US09345709B2

Reaction notes

Loading…