Lithium Hydroxide → (S)-3-methyl-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxylic acid

HRID 521568Notes

Reaction equation

HRID 521568 reaction equation
[CH3:1][C:2]1[N:6]2[N:7]=[C:8]([N:15]([CH3:24])[C@H:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:17])[CH:9]=[C:10]([C:11]([O:13]C)=[O:12])[C:5]2=[N:4][N:3]=1.[Li+].[OH-]>CO>[CH3:1][C:2]1[N:6]2[N:7]=[C:8]([N:15]([CH3:24])[C@H:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:17])[CH:9]=[C:10]([C:11]([OH:13])=[O:12])[C:5]2=[N:4][N:3]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 71115995(S)-methyl 3-methyl-6-(methyl (1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxylate

Product 1

HCID 71115949(S)-3-methyl-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxylic acidYield 86.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of compound (S)-methyl 3-methyl-6-(methyl (1-phenylethyl) amino)-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxylate (400 mg, 1.22 mmol) and LiOH (88 mg, 3.66 mmol) in MeOH (15 mL) was stirred at room temperature for 0.5 h and then concentrated in vacuum. The residue was dissolved with DCM (100 mL), adjusted pH to 3 with 2 N aq. HCl and washed with brine (20 mL). The organic layer was evaporated in vacuum to give product (S)-3-methyl-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxylic acid as a yellow solid (330 mg, 85%). 1H NMR (300 MHz, CDCl3) δ: 7.95 (s, 1H), 7.29˜7.42 (m, 5H), 5.83˜5.85 (s, 1H), 2.98 (s, 3H), 2.70 (s, 3H), 1.70 (d, 3H, J=6.6 Hz). LRMS (M+H+) m/z: calcd 312; found 312.

Workup

  1. concentrationconcentrated in vacuum
  2. dissolutionThe residue was dissolved with DCM (100 mL)
  3. washwashed with brine (20 mL)
  4. customThe organic layer was evaporated in vacuum

Sources & evidence

ORD record
ord-3936027913b64fb4bf0ed5e572bc8cb0
Source dataset
uspto-grants-2016_05
Patent number
US09328117B2

Reaction notes

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