Methylamine → HCID 90449306, compound

HRID 925501Notes

Reaction equation

HRID 925501 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][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=1.[CH3:25][NH2:26].[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:26][CH3:25])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 86714219HCID 86714219, compound

Product 1

HCID 90449306HCID 90449306, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

6-chloro-4-((3-(trifluoromethyl)phenyl)amino)-1,5-naphthyridine-3-carbaldehyde (0.75 g, 2.13 mmol) was dissolved in ethanol (20 mL), added 1.2 mL of a solution of methylamine in ethanol (concentration 27%), stirred at room temperature for 4 h, and then added sodium borohydride (0.82 g, 21.7 mmol) to the system, continued stirring at room temperature for 18 h. The reaction was quenched with a saturated aqueous solution of sodium carbonate, concentrated under reduced pressure to remove ethanol, extracted with 80 mL of dichloromethane, the organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain 0.77 g of the titled compound.

Workup

  1. customThe reaction was quenched with a saturated aqueous solution of sodium carbonate
  2. concentrationconcentrated under reduced pressure
  3. customto remove ethanol
  4. extractionextracted with 80 mL of dichloromethane
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d595a0d230394885977192633ca613ad
Source dataset
uspto-grants-2016_03
Patent number
US09284315B2

Reaction notes

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