Lithium Hydroxide → HCID 178456369, compound

HRID 2116900Notes

Reaction equation

HRID 2116900 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13](COCC[Si](C)(C)C)[C:12]([N:22]3[CH2:27][CH2:26][N:25]([C:28]4[C:33]([C:34]([F:37])([F:36])[F:35])=[CH:32][CH:31]=[CH:30][N:29]=4)[CH2:24][CH2:23]3)=[N:11][C:10]=2[C:38](OC)=[O:39])=[CH:5][CH:4]=1.[Li+].[OH-].[CH2:46]1[CH2:50]OC[CH2:47]1.O>>[CH:46]([N:22]1[CH2:27][CH2:26][N:25]([C:38]([C:10]2[N:11]=[C:12]([N:22]3[CH2:27][CH2:26][N:25]([C:28]4[C:33]([C:34]([F:35])([F:36])[F:37])=[CH:32][CH:31]=[CH:30][N:29]=4)[CH2:24][CH2:23]3)[NH:13][C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:42])([F:43])[F:1])=[CH:4][CH:5]=2)=[O:39])[CH2:24][CH2:23]1)([CH3:50])[CH3:47]

Participants

4

Reactant 3

HCID 3939Lithium HydroxideHCID 21881883Oxolane--water (1/1)HCID 58625828HCID 58625828, compound

Product 1

HCID 178456369HCID 178456369, compound

Procedure

A solution of methyl 5-(4-(trifluoromethyl)phenyl)-2-(4-(3-(trifluoromethyl)pyridin-2-yl)piperazin-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-4-carboxylate from step (d) above (500. mg, 0.794 mmol) in THF:H2O (5:1) was added LiOH (29 mg, 1.19 mmol, Aldrich) at 0° C. The mixture was stirred at RT for 16 h and the solvents were removed. The residue was dissolved in H2O (20 mL) and the aqueous solution was adjusted to pH ˜7. Then, the solvents were removed and the residue was purified on silica gel using ISCO Combiflash® system with EtOAc/Hexanes (1:4) as the eluant to give the title compound as a white solid. MS (ESI, positive ion) m/z: 616 (M+1).

Workup

  1. customthe solvents were removed
  2. dissolutionThe residue was dissolved in H2O (20 mL)
  3. customThen, the solvents were removed
  4. customthe residue was purified on silica gel using ISCO Combiflash® system with EtOAc/Hexanes (1:4) as the eluant

Sources & evidence

ORD record
ord-73dbc4abb9b24b0f8cc76bd7e4f15cb5
Source dataset
uspto-grants-2008_10
Patent number
US07439360B2

Reaction notes

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