Hydrochloric Acid → HCID 58318590, compound

HRID 473431Notes

Reaction equation

HRID 473431 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH:22]([N:24]3C(=O)C4C(=CC=CC=4)C3=O)[CH3:23])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[S:18]([CH3:21])(=[O:20])=[O:19])=[N:9]2)=[N:4][CH:3]=1.O.NN.Cl>CCO>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([CH:22]([NH2:24])[CH3:23])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[S:18]([CH3:21])(=[O:20])=[O:19])=[N:9]2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 58318599HCID 58318599, compound

Product 1

HCID 58318590HCID 58318590, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 2-(1-(7-fluoro-2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)ethyl) isoindoline-1,3-dione (1.2 g, 2.52 mmol in EtOH (40 mL) was added hydrazine hydrate (0.8 mL, 16.4 mmol) at 25° C. The reaction mixture was stirred for overnight at 25° C. The reaction mixture was acidified with 5 N hydrochloric acid and concentrated in vacuo. Water was added to residue and extracted with EtOAc. Aq. layer was basified with aq. NaOH solution and extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated in vacuo to give 1-(7-fluoro-2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)ethanamine: LC-MS (ESI) m/z 345.96 [M+H]+. It was carried on crude for next step.

Workup

  1. concentrationconcentrated in vacuo
  2. additionWater was added to residue
  3. extractionextracted with EtOAc
  4. extractionextracted with EtOAc
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c8af96a851ae4f0bbaac8b778219b8b5
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Reaction notes

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