Cyanogen Bromide → HCID 57986843, compound

HRID 871936Notes

Reaction equation

HRID 871936 reaction equation
[N:1]1([C:6]2[CH:24]=[CH:23][C:9]([O:10][CH2:11][C:12]3[N:13]=[C:14]([CH:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[S:15][CH:16]=3)=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].[N:31]#[C:32]Br>C(Cl)(Cl)Cl>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([O:10][CH2:11][C:12]3[N:13]=[C:14]([CH:17]4[CH2:18][CH2:19][N:20]([C:32]#[N:31])[CH2:21][CH2:22]4)[S:15][CH:16]=3)=[CH:23][CH:24]=2)[CH:5]=[N:4][N:3]=[N:2]1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 11430Potassium CarbonateHCID 57333784HCID 57333784, compound

Product 1

HCID 57986843HCID 57986843, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a mixture of 4-[4-(4-Tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidine (1.00 g, 2.92 mmol) and potassium carbonate (1.5 g, 10.9 mmol) in chloroform (25 mL) was added cyanogen bromide (0.371 g, 3.5 mmol). The slurry was refluxed for 48 hours then stirred at room temperature for an additional 48 hours. The reaction was filtered through a pad of celite, concentrated and chromatographed on silica gel (1:1 Hexanes/EtOAc) to afford the desired compound.

Workup

  1. temperatureThe slurry was refluxed for 48 hours
  2. filtrationThe reaction was filtered through a pad of celite
  3. concentrationconcentrated
  4. customchromatographed on silica gel (1:1 Hexanes/EtOAc)

Sources & evidence

ORD record
ord-f6e74dc3e55e471382d5e42a8a534eb7
Source dataset
uspto-grants-2015_03
Patent number
US08975258B2

Reaction notes

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