Water → HCID 46183722, compound

HRID 417062Notes

Reaction equation

HRID 417062 reaction equation
C([O:3][C:4](=[O:38])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH:13]([N:20]2[C:24]3[CH:25]=[C:26]([F:30])[C:27]([F:29])=[CH:28][C:23]=3[N:22]=[C:21]2[C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)[CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[CH:7][CH:6]=1)C.O.[OH-].[Li+].O>O1CCOCC1>[Cl:37][C:34]1[CH:33]=[CH:32][C:31]([C:21]2[N:20]([CH:13]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:12][O:11][C:8]3[CH:9]=[CH:10][C:5]([C:4]([OH:38])=[O:3])=[CH:6][CH:7]=3)[C:24]3[CH:25]=[C:26]([F:30])[C:27]([F:29])=[CH:28][C:23]=3[N:22]=2)=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 666192404-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-benzoic acid ethyl ester

Product 1

HCID 46183722HCID 46183722, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
100 °C

Procedure

To the solution of 0.22 g (0.4 mmol) 4-{2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-benzoic acid ethyl ester in 3 mL dioxane, 50 mg (1.2 mmol) lithium hydroxide monohydrate and 3 mL water were added and the solution was stirred for 2 h at 100° C. After cooling to room temperature dioxane was evaporated and 7.6 mL 1N hydrochloric acid was added under stirring. The resulting suspension was filtered, thoroughly washed with water and the filter cake dried under high vacuum to give the product as a white solid (94%). MS (Turbo Spray): m/z=509.2 [M+H].

Workup

  1. customwas evaporated
  2. addition7.6 mL 1N hydrochloric acid was added
  3. stirringunder stirring
  4. filtrationThe resulting suspension was filtered
  5. washthoroughly washed with water
  6. customthe filter cake dried under high vacuum

Sources & evidence

ORD record
ord-da7a8a149c824d9e9c5a95248d491911
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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