HCID 67133043, compound → HCID 178519289, compound

HRID 545435Notes

Reaction equation

HRID 545435 reaction equation
C([N:8]1[CH:12]=[N:11][C:10]([C:13]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][CH:19]=3)[N:15]([CH:29]3[CH2:31][CH2:30]3)[C:14]=2[C:32]([N:34]2[CH2:39][CH2:38][CH:37]([N:40]3[CH2:44][CH2:43][CH2:42][CH2:41]3)[CH2:36][CH2:35]2)=[O:33])=[N:9]1)C1C=CC=CC=1.[H][H]>[Pd].CO.Cl>[CH:29]1([N:15]2[C:14]([C:32]([N:34]3[CH2:35][CH2:36][CH:37]([N:40]4[CH2:41][CH2:42][CH2:43][CH2:44]4)[CH2:38][CH2:39]3)=[O:33])=[C:13]([C:10]3[N:11]=[CH:12][NH:8][N:9]=3)[N:17]=[C:16]2[C:18]2[CH:19]=[CH:20][C:21]([O:24][C:25]([F:27])([F:26])[F:28])=[CH:22][CH:23]=2)[CH2:31][CH2:30]1

Participants

6

Reactant 2

HCID 67133043HCID 67133043, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 178519289HCID 178519289, compoundYield 77.6%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.07 g (0.1 mmol) of [5-(1-benzyl-1H-[1,2,4]triazol-3-yl)-3-cyclopropyl-2-(4-trifluoromethoxy-phenyl)-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (intermediate 12) and a generous spatula of 10% palladium on activated charcoal in 1 ml of MeOH made acidic by addition of a few drops of 25% HCl was stirred under one atmosphere of hydrogen for 16 h. Then, the mixture was filtered over Hyflo, concentrated and the residue taken up in CH2Cl2. The organic phase was washed with saturated sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. Purification by flash column chromatography [CH2Cl2/MeOH 9:1 to 8:2] afforded 0.04 g (64%) of the title compound as a colorless amorphous solid. MS: 516.2 (MH+).

Workup

  1. filtrationThen, the mixture was filtered over Hyflo
  2. concentrationconcentrated
  3. washThe organic phase was washed with saturated sodium hydrogen carbonate solution
  4. dry with materialdried with sodium sulphate
  5. concentrationconcentrated
  6. customPurification by flash column chromatography [CH2Cl2/MeOH 9:1 to 8:2]

Sources & evidence

ORD record
ord-d5a19051cf1a492887ebcb85789d54ab
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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