HCID 57541149, compound → HCID 25152895, compound

HRID 545431Notes

Reaction equation

HRID 545431 reaction equation
[CH:1]1([N:4]2[C:8]([C:9]([N:11]3[CH2:16][CH2:15][CH:14]([N:17]4[CH2:21][CH2:20][CH2:19][CH2:18]4)[CH2:13][CH2:12]3)=[O:10])=[C:7]([C:22]3[CH:23]=[N:24][C:25](SC)=[N:26][CH:27]=3)[N:6]=[C:5]2[C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]([F:40])([F:39])[F:38])=[CH:32][CH:31]=2)[CH2:3][CH2:2]1>CCO.[Ni]>[CH:1]1([N:4]2[C:8]([C:9]([N:11]3[CH2:16][CH2:15][CH:14]([N:17]4[CH2:18][CH2:19][CH2:20][CH2:21]4)[CH2:13][CH2:12]3)=[O:10])=[C:7]([C:22]3[CH:23]=[N:24][CH:25]=[N:26][CH:27]=3)[N:6]=[C:5]2[C:30]2[CH:31]=[CH:32][C:33]([O:36][C:37]([F:38])([F:39])[F:40])=[CH:34][CH:35]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 57541149HCID 57541149, compound

Product 1

HCID 25152895HCID 25152895, compoundYield 40.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 0.08 g (0.14 mmol) of [3-cyclopropyl-5-(2-methylsulfanyl-pyrimidin-5-yl)-2-(4-trifluoromethoxy-phenyl)-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 88) in 1 ml of EtOH was added a generous spatula of Rainey nickel. The mixture was stirred for 15 minutes after which time the reaction was filtered over Hyflo and concentrated. Purification by flash column chromatography [CH2Cl2/MeOH 8:2] afforded 0.03 g (38%) of the title compound as a colorless amorphous solid. MS: 527.2 (MH+)

Workup

  1. filtrationwas filtered over Hyflo
  2. concentrationconcentrated
  3. customPurification by flash column chromatography [CH2Cl2/MeOH 8:2]

Sources & evidence

ORD record
ord-abbaa59542cc4a0b8533e40e8d391413
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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