Formaldehyde → HCID 66576311, compound

HRID 2208764Notes

Reaction equation

HRID 2208764 reaction equation
[CH:1]1([N:6]([CH3:33])[C:7]2[C:8]([CH3:32])=[C:9]([CH:23]=[C:24]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)[CH:25]=2)[C:10]([NH:12][CH2:13][C:14]2[C:15](=[O:22])[NH:16][C:17]([CH3:21])=[CH:18][C:19]=2[CH3:20])=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.C=O.[C:36]([BH3-])#N.[Na+]>CO>[CH:1]1([N:6]([CH3:33])[C:7]2[C:8]([CH3:32])=[C:9]([CH:23]=[C:24]([N:26]3[CH2:31][CH2:30][N:29]([CH3:36])[CH2:28][CH2:27]3)[CH:25]=2)[C:10]([NH:12][CH2:13][C:14]2[C:15](=[O:22])[NH:16][C:17]([CH3:21])=[CH:18][C:19]=2[CH3:20])=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 66576310HCID 66576310, compound

Product 1

HCID 66576311HCID 66576311, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-(Cyclopentyl(methyl)amino)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-5-(piperazin-1-yl)benzamide (free base) (0.100 g, 0.223 mmol) was dissolved in methanol (5 mL) and cooled to 0° C. before formalin (0.033 g, 1.1 mL, 2.23 mmol) was added. The resulting reaction mixture was stirred at same temperature for 30 minutes. Sodium cyanoborohydride (0.013 g, 0.22 mmol) was added to above reaction mixture and stirred at room temperature for 4 h. After completion, solvent was removed under reduced pressure and water added to the residue, with extraction carried out using DCM. The combined organic layers were dried, concentrated and purified by column chromatography to provide desired 3-(cyclopentyl(methyl)amino)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-2-methyl-5-(4-methylpiperazin-1-yl)benzamide (0.037 g, 36%).

Workup

  1. additionwas added
  2. customThe resulting reaction mixture
  3. stirringstirred at room temperature for 4 h
  4. customAfter completion, solvent was removed under reduced pressure and water
  5. additionadded to the residue, with extraction
  6. customThe combined organic layers were dried
  7. concentrationconcentrated
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-3853f1bef183497f803f40a35848c8dd
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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