Hydrochloric Acid → HCID 46184941, compound

HRID 417092Notes

Reaction equation

HRID 417092 reaction equation
C([O:3][C:4](=[O:40])[CH2:5][O:6][C:7]1[CH:8]=[N:9][C:10]([O:13][CH2:14][CH:15]([N:22]2[C:26]3[CH:27]=[C:28]([F:32])[C:29]([F:31])=[CH:30][C:25]=3[N:24]=[C:23]2[C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)[CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:11][CH:12]=1)C.[OH-].[Na+].Cl>O1CCCC1>[Cl:39][C:36]1[CH:37]=[CH:38][C:33]([C:23]2[N:22]([CH:15]([CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)[CH2:14][O:13][C:10]3[N:9]=[CH:8][C:7]([O:6][CH2:5][C:4]([OH:40])=[O:3])=[CH:12][CH:11]=3)[C:26]3[CH:27]=[C:28]([F:32])[C:29]([F:31])=[CH:30][C:25]=3[N:24]=2)=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66619272HCID 66619272, compound

Product 1

HCID 46184941HCID 46184941, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 0.18 g (0.32 mmol) (6-{2-[2-(4-chloro-phenyl)-5,6-difluoro-benzoimidazol-1-yl]-2-cyclohexyl-ethoxy}-pyridin-3-yloxy)-acetic acid ethyl ester in 2 mL tetrahydrofuran 2 mL water and 0.13 mL (0.77 mmol) 32% aqueous sodium hydroxide solution were added. The mixture was stirred at 75° C. for 1.5 h and then poured on 20 mL 1M aqueous hydrochloric acid. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with water and brine, dried over magnesium sulfate and evaporated to dryness. The residue was suspended in a mixture of acetonitrile and water, filtered and washed with acetonitrile to give the desired product as a white solid (61%). MS (Turbo Spray): m/z=542.3 [M+H].

Workup

  1. extractionThe aqueous layer was extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness
  5. additionThe residue was suspended in a mixture of acetonitrile and water
  6. filtrationfiltered
  7. washwashed with acetonitrile

Sources & evidence

ORD record
ord-b1b25ee005dc4b8097e8bc3cb7bbe992
Source dataset
uspto-grants-2012_01
Patent number
US08088930B2

Reaction notes

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