Water → HCID 178514065, compound

HRID 1023458Notes

Reaction equation

HRID 1023458 reaction equation
COC1C=C(OC)C=CC=1C[N:6]1[C:10]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]([NH2:20])=[O:19])[CH:12]=2)=[C:9]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[N:8]=[CH:7]1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+].O>C(Cl)Cl>[F:27][C:24]1[CH:25]=[CH:26][C:21]([C:9]2[N:8]=[CH:7][NH:6][C:10]=2[C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]([NH2:20])=[O:19])[CH:12]=2)=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 69082609HCID 69082609, compound

Product 1

HCID 178514065HCID 178514065, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of {4-[3-(2,4-Dimethoxy-benzyl)-5-(4-fluoro-phenyl)-3H-imidazol-4-yl]-pyridin-2-yl}-urea (Example 51, 15 mg, 0.034 mmol) in DCM (1.0 mL) is added trifluoroacetic acid (0.1 mL). The reaction mixture is stirred for 6.5 days at room temperature before saturated NaHCO3 aqueous solution (2 mL) is added along with water (10 ml). The mixture is extracted with EtOAc (3×20 mL) and the organic layers are combined, dried and concentrated to give the crude product. Purification by silica flash column chromatography using 10% MeOH in DCM affords 9.7 mg of the titled product.

Workup

  1. extractionThe mixture is extracted with EtOAc (3×20 mL)
  2. customdried
  3. concentrationconcentrated
  4. customto give the crude product
  5. customPurification by silica flash column chromatography

Sources & evidence

ORD record
ord-1e5595d4ddb74b1e9bee09f1afbac5dc
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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