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 1479950Notes

Reaction equation

HRID 1479950 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

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 887MethanolSolvent

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-14e891d38b7c4c5996b13137e992d9d2
Source dataset
uspto-grants-2016_08
Patent number
US09409871B2

Reaction notes

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