Hydrochloric Acid → HCID 178488855, compound

HRID 1161309Notes

Reaction equation

HRID 1161309 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([NH:12][C:13](=[O:42])[CH:14]([CH:36]2[CH2:41][CH2:40][CH2:39][CH2:38][CH2:37]2)[N:15]2[C:19]3[CH:20]=[C:21]([F:25])[C:22]([F:24])=[CH:23][C:18]=3[N:17]=[C:16]2[C:26]2[C:27]([O:34][CH3:35])=[N:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].Cl>C(#N)C.O>[CH:36]1([CH:14]([N:15]2[C:19]3[CH:20]=[C:21]([F:25])[C:22]([F:24])=[CH:23][C:18]=3[N:17]=[C:16]2[C:26]2[C:27]([O:34][CH3:35])=[N:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)[C:13]([NH:12][C@H:9]2[CH2:8][CH2:7][C@H:6]([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]2)=[O:42])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68645904HCID 68645904, compound

Product 1

HCID 178488855HCID 178488855, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-{2-cyclohexyl-2-[2-(2,6-dimethoxy-pyridin-3-yl)-5,6-difluoro-benzoimidazol-1-yl]-acetylamino}-cyclohexanecarboxylic acid ethyl ester (350 mg, 0.60 mmol, 1.0 equiv) in a mixture of acetonitrile/water (2:1, 5 mL) was added a solution of aqueous 6 M NaOH (0.3 mL, 1.80 mmol, 3.0 equiv) and the reaction mixture heated by microwave irradiation to 100° C. for 30 min. The solvent was removed under reduced pressure and the crude reaction mixture adjusted to pH=3 by addition of a solution of 1 M HCl and the aqueous layer extracted with a mixture of dichloromethane/isopropanol (4:1). The combined organic phases were dried over MgSO4, concentrated by evaporation under reduced pressure and the crude material purified over a short silica column eluting with a gradient of dichloromethane/methanol yielding 0.31 g (93%) of the title compound. MS (ES+): 558 (M+H).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude reaction mixture
  3. extractionthe aqueous layer extracted with a mixture of dichloromethane/isopropanol (4:1)
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated by evaporation under reduced pressure
  6. customthe crude material purified over a short silica column
  7. washeluting with a gradient of dichloromethane/methanol yielding 0.31 g (93%) of the title compound

Sources & evidence

ORD record
ord-5cf0a0a0e836430e8308d2bde1b603d9
Source dataset
uspto-grants-2010_10
Patent number
US07816540B2

Reaction notes

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