Sodium Hydroxide → HCID 11575876, compound

HRID 1821411Notes

Reaction equation

HRID 1821411 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]/[C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][N:23]=3)=[C:16]([NH:31][C:32]([C:34]3[S:35][CH:36]=[CH:37][C:38]=3[CH3:39])=[O:33])[CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.C(O)C.[OH-].[Na+]>C(O)C>[NH:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22](/[CH:21]=[CH:20]/[C:17]2[CH:18]=[CH:19][C:14]([N:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[CH:15][C:16]=2[NH:31][C:32]([C:34]2[S:35][CH:36]=[CH:37][C:38]=2[CH3:39])=[O:33])=[N:23]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21887872Ethanol hydrochlorideHCID 69000275HCID 69000275, compound

Product 1

HCID 11575876HCID 11575876, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(E)-4-{4-[2-(1H-indazol-3-yl)vinyl]-3-[(3-methylthiophene-2-carbonyl)amino]phenyl}piperazine-1-carboxylic acid tert-butyl ester (51 mg, 0.09 mmol) obtained in Step 4 was dissolved in ethanol (2.0 ml) and the solution was added with 1 mol/L hydrogen chloride-ethanol solution (1.0 mL), followed by stirring for 1 hour. To the reaction mixture under ice-cooling, 6 mol/L aqueous sodium hydroxide solution was added to neutralize the mixture. Then the mixture was filtered. The filtrate was added with saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was triturated in methanol to obtain Compound 274 (22 mg, 55%).

Workup

  1. temperatureTo the reaction mixture under ice-cooling
  2. filtrationThen the mixture was filtered
  3. additionThe filtrate was added with saturated aqueous sodium hydrogencarbonate solution
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was triturated in methanol

Sources & evidence

ORD record
ord-662c3159b4eb4668833f0ef7e0ec8683
Source dataset
uspto-grants-2009_10
Patent number
US07605272B2

Reaction notes

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