Methylamine → HCID 90449220, compound

HRID 925511Notes

Reaction equation

HRID 925511 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]([N:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)=[C:17]([C:34]([F:37])([F:36])[F:35])[CH:16]=1.[CH3:38][NH2:39].[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:39][CH3:38])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:31])[CH3:32])=[O:28])[CH2:23][CH2:22]2)=[C:17]([C:34]([F:36])([F:35])[F:37])[CH:16]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 86714224HCID 86714224, compound

Product 1

HCID 90449220HCID 90449220, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

tert-butyl 4-(4-((6-chloro-3-formyl-1,5-naphthyridin-4-yl)amino)-2-(trifluoromethyl)phenyl)piperazine-1-carboxylate (0.223 g, 0.416 mmol) was dissolved in 20 mL of ethanol, added 0.3 mL of a solution of methylamine in ethanol (concentration 27%), and stirred at room temperature for 24 h. After confirming a disappearance of the raw materials by LC-MS, to the system added sodium borohydride (0.09 g, 2.38 mmol), 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 100 mL dichloromethane. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to give 0.193 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 100 mL dichloromethane
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c4a8c61098df4b5ebbfcbdfe32295cf3
Source dataset
uspto-grants-2016_03
Patent number
US09284315B2

Reaction notes

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