Lithium Hydroxide → HCID 44481091, compound

HRID 538162Notes

Reaction equation

HRID 538162 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([C:11]2[NH:15][C:14]3[CH:16]=[C:17]([S:21]([CH2:23][CH3:24])=[O:22])[C:18]([Cl:20])=[CH:19][C:13]=3[N:12]=2)[CH:10]=1)=[O:5])C.C1COCC1.[OH-].[Li+]>O>[Cl:20][C:18]1[C:17]([S:21]([CH2:23][CH3:24])=[O:22])=[CH:16][C:14]2[NH:15][C:11]([N:9]3[CH:10]=[C:6]([C:4]([OH:5])=[O:3])[CH:7]=[N:8]3)=[N:12][C:13]=2[CH:19]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 66937031HCID 66937031, compound

Product 1

HCID 44481091HCID 44481091, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

To a solution of 1-(5-chloro-6-ethanesulfinyl-1H-benzoimidazol-2-yl)-1H-pyrazole-4-carboxylic acid ethyl ester (100 mg, 0.273 mmol), THF (1.0 mL), and water (0.33 mL) was added lithium hydroxide (31.3 mg, 0.818 mmol). The mixture was sonicated briefly, and stirred at 23° C. for 56 h. The solvent was evaporated, water was added, and the resulting solution was acidified to pH 1 with 1M aq. HCl. The precipitate was collected to yield the titled compound (79.1 mg, 85% yield). MS (ESI/CI): mass calcd. for C13H11ClN4O3S, 338.0; m/z found, 339.0 [M+H]+. 1H NMR (400 MHz, DMSO-d6, tautomeric broadening): 13.88 (br s, 1H), 13.01 (br s, 1H), 8.94 (s, 1H), 8.40 (s, 1H), 8.03-7.55 (m, 2H), 3.23-3.11 (m, 1H), 2.89-2.78 (m, 1H), 1.08 (t, J=7.4 Hz, 3H).

Workup

  1. customThe mixture was sonicated briefly
  2. customThe solvent was evaporated
  3. additionwater was added
  4. customThe precipitate was collected

Sources & evidence

ORD record
ord-77dbadc4c62e4561b99eda9af23ee9d5
Source dataset
uspto-grants-2014_10
Patent number
US08865713B2

Reaction notes

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