Triethylamine → HCID 178521528, compound

HRID 1986132Notes

Reaction equation

HRID 1986132 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([SH:6])=[N:2]1.C(N(CC)CC)C.Br[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][C:26]2[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=2[F:33])=[CH:20][CH:19]=1)=[O:17]>ClCCl>[F:32][C:31]1[CH:30]=[CH:29][CH:28]=[C:27]([F:33])[C:26]=1[CH2:25][O:24][C:21]1[CH:20]=[CH:19][C:18]([C:16](=[O:17])[CH2:15][S:6][C:3]2[N:4]=[CH:5][NH:1][N:2]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 219644702-Bromo-1-(4-(2,6-difluorobenzyloxy)phenyl)-1-EthanoneHCID 178527894HCID 178527894, compound

Product 1

HCID 178521528HCID 178521528, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1H-1,2,4-Triazole-3-thiol (0.250 g, 2.4 mmol) and triethylamine (2.50 g, 2.4 mmol) in dry dichloromethane (20 ml) was added 2-Bromo-1-(4-(2,6-difluorobenzyloxy)phenyl)-1-Ethanone (Step B, 0.851 g, 2.4 mmol) in dry dichloromethane (5 ml) at room temperature. The reaction mixture was stirred for 50 minutes and then concentrated in vacuo. The crude residue was taken in EtOAc and washed with 0.1M HCl, and brine. The organic layer was dried over Na2SO4, filtered, concentrated and purified by flash chromatography on silica gel column (chloroform:methanol, 9:1) to provide the title compound.

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed with 0.1M HCl, and brine
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography on silica gel column (chloroform:methanol, 9:1)

Sources & evidence

ORD record
ord-43e77dd87cc54ff5867bca0b579e4708
Source dataset
uspto-grants-2009_06
Patent number
US07547802B2

Reaction notes

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