Lithium hydroxide, monohydrate → HCID 59186125, compound

HRID 1671340Notes

Reaction equation

HRID 1671340 reaction equation
C([O:3][C:4]([C:6]1[C:7]([CH3:23])=[N:8][N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:15]=3[CH3:21])=[C:12]([CH3:22])[O:11][C:10]=12)=[O:5])C.O.[OH-].[Li+]>CCO.O>[CH3:21][C:15]1[CH:16]=[C:17]([CH3:20])[CH:18]=[CH:19][C:14]=1[C:13]1[N:9]2[N:8]=[C:7]([CH3:23])[C:6]([C:4]([OH:5])=[O:3])=[C:10]2[O:11][C:12]=1[CH3:22]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 67212603HCID 67212603, compound

Product 1

HCID 59186125HCID 59186125, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

A stirred mixture of 3-(2,4-dimethyl-phenyl)-2,6-dimethyl-pyrazolo[5,1-b]oxazole-7-carboxylic acid ethyl ester (224 mg, 0.72 mmol, 1 eq.) and lithium hydroxide monohydrate (150 mg, 3.59 mmol, 5 eq.) in EtOH (4 ml) and water (2 ml) is heated at 45° C. for 14 h. The reaction mixture is cooled to RT then concentrated under reduced pressure. The residue is dissolved in water and the resulting aqueous solution is neutralized using 2M HCl in water (1.8 ml). The resulting precipitate is filtered, washed with water and dried under vacuum to yield the title compound as a white solid. The crude compound is used without further purification. HPLC: AtRet=2.12; MS: m/z 285.2 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 2.20 (s, 3H), 2.33 (s, 3H), 2.36 (s, 3H), 2.39 (s, 3H), 7.16 (m, 1H), 7.24 (br. s., 1H), 7.31 (m, 1H), 12.30 (br. s., 1H).

Workup

  1. temperatureThe reaction mixture is cooled to RT
  2. concentrationthen concentrated under reduced pressure
  3. dissolutionThe residue is dissolved in water
  4. filtrationThe resulting precipitate is filtered
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-7b02fc735fe0430e8ead684987259029
Source dataset
uspto-grants-2011_08
Patent number
US07994203B2

Reaction notes

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