Methylamine → HCID 89589821, compound

HRID 925506Notes

Reaction equation

HRID 925506 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([CH:12]=O)=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:25])([CH3:24])[C:22]#[N:23])=[CH:17][CH:16]=1.[CH3:26][NH2:27].[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([CH2:12][NH:27][CH3:26])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:25])([CH3:24])[C:22]#[N:23])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 86714227HCID 86714227, compound

Product 1

HCID 89589821HCID 89589821, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-(4-((6-chloro-3-formyl-1,5-naphthyridin-4-yl)amino)phenyl)-2-methylpropionitrile (2.5 g, 7.1 mmol) was dissolved in ethanol (100 mL), added 3 mL of a solution of methylamine in ethanol (concentration 27%), stirred at room temperature for 10 h. Then, to the system added sodium borohydride (1.5 g, 3.97 mol), continued stirring at room temperature for 18 h, and the reaction was quenched with a saturated aqueous solution of sodium carbonate. Concentrated under reduced pressure to remove ethanol, extracted with 150 mL of dichloromethane, the organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to give 2.2 g of a solid.

Workup

  1. stirringcontinued stirring at room temperature for 18 h
  2. customthe reaction was quenched with a saturated aqueous solution of sodium carbonate
  3. concentrationConcentrated under reduced pressure
  4. customto remove ethanol
  5. extractionextracted with 150 mL of dichloromethane
  6. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4d43ebdb05aa45558963324f8c0aae26
Source dataset
uspto-grants-2016_03
Patent number
US09284315B2

Reaction notes

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