Ethanol → HCID 90449299, compound

HRID 925505Notes

Reaction equation

HRID 925505 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]([C:12](OCC)=[O:13])=[C:5]2[NH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:27]#[N:28])([CH3:26])[CH3:25])=[CH:20][CH:19]=1.C(O)C.[BH4-].[Na+]>ClCCl>[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][OH:13])=[C:5]2[NH:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([CH3:26])([CH3:25])[C:27]#[N:28])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 89589794HCID 89589794, compound

Product 1

HCID 90449299HCID 90449299, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 6-chloro-4-((4-(2-cyanopropan-2-yl)phenyl)amino)-1,5-naphthyridine-3-carboxylate (8.1 g, 20.5 mmol) was added to a mixed solvent of ethanol (120 mL) and dichloromethane (12 mL), to the system added sodium borohydride (5.4 g, 143 mmol) in batches, stirred at room temperature for 24 h, ethanol was removed under reduced pressure, adjusted pH of the solution to be neutral with 1 N dilute hydrochloric acid and extracted with 200 mL of ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the resulting 9.0 g of a crude solid was used directly in the next step.

Workup

  1. customethanol was removed under reduced pressure
  2. extractionextracted with 200 mL of ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-18fea9da020544a79a7985eeb124ac16
Source dataset
uspto-grants-2016_03
Patent number
US09284315B2

Reaction notes

Loading…