Sodium Hydroxide → HCID 67399735, compound

HRID 70603Notes

Reaction equation

HRID 70603 reaction equation
O.NN.[CH:4]1([C:7]2[CH:8]=[CH:9][C:10](/[C:15](/[C:30]3[CH:35]=[CH:34][C:33]([S:36][CH3:37])=[CH:32][CH:31]=3)=[CH:16]/[CH2:17][CH2:18][N:19]3C(=O)C4C(=CC=CC=4)C3=O)=[N:11][C:12]=2[O:13][CH3:14])[CH2:6][CH2:5]1.[OH-].[Na+]>C(O)C>[CH:4]1([C:7]2[CH:8]=[CH:9][C:10](/[C:15](/[C:30]3[CH:35]=[CH:34][C:33]([S:36][CH3:37])=[CH:32][CH:31]=3)=[CH:16]/[CH2:17][CH2:18][NH2:19])=[N:11][C:12]=2[O:13][CH3:14])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 674002742-{(3E)-4-(5-cyclopropyl-6-methoxypyridin-2-yl)-4-[4-(methylsulfanyl)phenyl]but-3-en-1-yl}-1H-isoindole-1,3(2H)-dione

Product 1

HCID 67399735HCID 67399735, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

Hydrazine monohydrate (1 mL) was added to a solution of 2-{(3E)-4-(5-cyclopropyl-6-methoxypyridin-2-yl)-4-[4-(methylsulfanyl)phenyl]but-3-en-1-yl}-1H-isoindole-1,3(2H)-dione (320 mg) in ethanol (4 mL), and the mixture was stirred at 95° C. for one hour. The reaction solution was poured into a 3 M sodium hydroxide solution, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered, after which the solvent was evaporated under reduced pressure to give (3E)-4-(5-cyclopropyl-6-methoxypyridin-2-yl)-4-[4-(methylsulfanyl)phenyl]but-3-en-1-amine as a colorless amorphous (225 mg, 97%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customafter which the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-dbf7988bd3ec4d628f3d942f5381f4fb
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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