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Sodium Hydroxide → (R)-4-[6-(4-fluoro-phenyl)-4,5-dimethyl-pyridazin-3-yl]-2-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-carboxylic acid

HRID 447075
Notes
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Reaction equation

HRID 447075 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[CH:7][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[N:18]=[N:19][C:20]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=4)=[C:21]([CH3:24])[C:22]=3[CH3:23])[CH2:13][C@H:12]2[CH3:32])=[N:9][CH:10]=1)=[O:4].[OH-].[Na+]>CO>[F:31][C:28]1[CH:29]=[CH:30][C:25]([C:20]2[N:19]=[N:18][C:17]([N:14]3[CH2:15][CH2:16][N:11]([C:8]4[CH:7]=[N:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][N:9]=4)[C@H:12]([CH3:32])[CH2:13]3)=[C:22]([CH3:23])[C:21]=2[CH3:24])=[CH:26][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67179891(R)-4-[6-(4-fluoro-phenyl)-4,5-dimethyl-pyridazin-3-yl]-2-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-carboxylic acid methyl ester

Product 1

HCID 68571886(R)-4-[6-(4-fluoro-phenyl)-4,5-dimethyl-pyridazin-3-yl]-2-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-carboxylic acidYield 122.9%

Reagents, catalysts & solvents 1

HCID 887Methanol
Solvent

Procedure

To a solution of example 6 (0.74 g, 1.31 mmol) and methanol (10 mL) is added sodium hydroxide (100 mg). The mixture is stirred at room temperature overnight. Solvent is removed and the residue is dissolved in water and acidified with 3 N HCl to pH about 7, and extracted with ethyl acetate. The ethyl acetate layer is concentrated to afford the title compound (0.68 g, 96%) as a yellow solid.

Workup

  1. customSolvent is removed
  2. dissolutionthe residue is dissolved in water
  3. extractionextracted with ethyl acetate
  4. concentrationThe ethyl acetate layer is concentrated

Sources & evidence

ORD record
ord-d58b8392dc4c434cb38d77c9c652eac2
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08481542B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes