Sodium Hydroxide → HCID 178519285, compound

HRID 545436Notes

Reaction equation

HRID 545436 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.[OH-:41].[Na+]>CS(C)=O>[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]([OH:41])=[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

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57541149HCID 57541149, compound

Product 1

HCID 178519285HCID 178519285, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 0.06 g (0.1 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) and 0.1 ml of 6M sodium hydroxide solution in 0.5 ml of DMSO was heated to 100° C. for 3 h. The DMSO was removed using an Isolute SPE 103 cartridge, and the crude product purified by preparative HPLC affording 0.01 g (22%) of the title compound as a colorless amorphous solid. MS: 543.2 (MH+).

Workup

  1. customThe DMSO was removed
  2. customthe crude product purified by preparative HPLC

Sources & evidence

ORD record
ord-eb864bc54b874a9497174acf07966fb2
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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