Lithium hydroxide, monohydrate → HCID 59179705, compound

HRID 2381867Notes

Reaction equation

HRID 2381867 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][C:7]2[C:11](=[O:12])[N:10]([C:13]3[S:14][C:15]([C:19]([O:21]C)=[O:20])=[C:16]([CH3:18])[N:17]=3)[NH:9][C:8]=2[CH3:23])=[CH:4][CH:3]=1.O.[OH-].[Li+]>O1CCCC1.O>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][C:7]2[C:11](=[O:12])[N:10]([C:13]3[S:14][C:15]([C:19]([OH:21])=[O:20])=[C:16]([CH3:18])[N:17]=3)[NH:9][C:8]=2[CH3:23])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59179663HCID 59179663, compound

Product 1

HCID 59179705HCID 59179705, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(4-(4-chlorobenzyl)-3-methyl-5-oxo-2,5-dihydro-1H-pyrazol-1-yl)-4-methylthiazole-5-carboxylate (0.22 g, 0.57 mmol) in a mixture of tetrahydrofuran (8 mL) and water (2 mL) was added lithium hydroxide monohydrate (0.12 g, 2.88 mmol). The reaction mixture was heated to reflux for 3 hours. The solvent was removed in vacuo, and the residue was neutralized to pH 4˜5 with 10% hydrochloric acid. The resulting precipitate was collected by filtration and dried to afford the title compound in 53% yield (0.11 g): 1H NMR (300 MHz, DMSO-d6) δ 12.29 (br s, 1H), 7.27 (d, J=8.5 Hz, 2H), 7.21 (d, J=8.5 Hz, 2H), 3.52 (s, 2H), 2.56 (s, 3H), 2.14 (s, 3H); MS (ES+) m/z 364.1 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe solvent was removed in vacuo
  4. filtrationThe resulting precipitate was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-820061eb2c4e4c7c91d1d1a22947e321
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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