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

HRID 521563Notes

Reaction equation

HRID 521563 reaction equation
C[O:2][C:3]([C:5]1[C:6]2[N:7]([C:21]([CH3:24])=[N:22][N:23]=2)[N:8]=[C:9]([N:11]([CH3:20])[C@H:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH3:13])[CH:10]=1)=[O:4].[Li+].[OH-]>CO>[CH3:24][C:21]1[N:7]2[N:8]=[C:9]([N:11]([CH3:20])[C@H:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH3:13])[CH:10]=[C:5]([C:3]([OH:4])=[O:2])[C:6]2=[N:23][N:22]=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 85.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-methyl-3-methyl-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxylate (400 mg, 1.22 mmol) in MeOH (15 mL) was added a 1M aqueous solution of LiOH (3.66 mL, 3.66 mmol). After 30 min, the organic solvent was removed under reduced pressure, and the pH of the aqueous layer was adjusted to pH=3 with 2N HCl, extracted with CH2Cl2 (3×50 mL). The combined organic layers were concentrated to give the (S)-3-methyl-6-(methyl(1-phenylethyl)amino)-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxylic acid (325 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, J=6.6 Hz, 3H), LRMS [M+H]+: 311 m/z.

Workup

  1. customthe organic solvent was removed under reduced pressure
  2. extractionextracted with CH2Cl2 (3×50 mL)
  3. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-7a13c944e5b64d1c9453f6f782b46bca
Source dataset
uspto-grants-2016_05
Patent number
US09328117B2

Reaction notes

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