Hydrochloric Acid → HCID 44198099, compound

HRID 1161312Notes

Reaction equation

HRID 1161312 reaction equation
C([O:3][C:4](=[O:39])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12](=[O:38])[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+].Cl>O1CCOCC1.O>[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)[C:12]([NH:11][C:8]3[CH:9]=[CH:10][C:5]([C:4]([OH:39])=[O:3])=[CH:6][CH:7]=3)=[O:38])[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

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 686454934-{2-[2-(4-Chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-benzoic acid ethyl ester2×

Product 1

HCID 44198099HCID 44198099, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To the solution of 4-{2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-acetylamino}-benzoic acid ethyl ester (intermediate d) in 25 ml dioxan, 25 ml water and 0.57 g (13.6 mmol) lithium hydroxide monohydrate were added. The solution was stirred for 2 h at 100° C. After cooling to room temperature, 16 ml 1M aqueous hydrochloric acid were added upon stirring. The suspension was filtered, the filter cake washed with water and dried under high vacuum to give 2.46 g (99%) of the desired compound as colorless solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringupon stirring
  3. filtrationThe suspension was filtered
  4. washthe filter cake washed with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-638bbccda12a43b297b9508f6d02ce6b
Source dataset
uspto-grants-2010_10
Patent number
US07816540B2

Reaction notes

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