Pyrazole → HCID 66835677, compound

HRID 2404425Notes

Reaction equation

HRID 2404425 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]([O:18][CH:19]2[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]2)[C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH:5]=[CH:6][CH:7]=1.[NH:26]1[CH:30]=[CH:29][CH:28]=[N:27]1.[C:31](=[O:34])([O-:33])[O-].[Cs+].[Cs+].CN(C)C=[O:40]>[Cu]I>[C:19]([OH:18])(=[O:40])[C:31]([OH:33])=[O:34].[CH3:25][N:22]1[CH2:23][CH2:24][CH:19]([O:18][CH:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([N:26]3[CH:30]=[CH:29][CH:28]=[N:27]3)[CH:3]=2)[C:9]2[S:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)[CH2:20][CH2:21]1

Participants

6

Reactant 4

HCID 1048PyrazoleHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 66835733HCID 66835733, compound

Product 1

HCID 66835677HCID 66835677, compound

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Conditions

Temperature
120 °C

Procedure

To a solution of 2-[(3-Bromophenyl)(1-methylpiperidin-4-yloxy)methyl]benzothiazole (208 mg) in N,N-dimethylformamide (1 mL) are added pyrazole (68 mg), cesium carbonate (401 mg) and copper(I) iodide (19 mg). The tube is evacuated, filled with argon and sealed. After stirring at 120° C. for 48 h, the mixture is diluted with water and ammonia solution then extracted with ethyl acetate. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 100/0/0 to 95/5/0.5). The residue is added to a solution of oxalic acid (1 molar equivalent) and the residual precipitate is filtered and dried to afford 2-[(1-methylpiperidin-4-yloxy)(3-pyrazol-1-ylphenyl)methyl]benzothiazole oxalate melting at 89° C.

Workup

  1. customThe tube is evacuated
  2. additionfilled with argon
  3. customsealed
  4. additionthe mixture is diluted with water and ammonia solution
  5. extractionthen extracted with ethyl acetate
  6. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 100/0/0 to 95/5/0.5)
  9. additionThe residue is added to a solution of oxalic acid (1 molar equivalent)
  10. filtrationthe residual precipitate is filtered
  11. customdried

Sources & evidence

ORD record
ord-1e11e38b032545b1b0a5d1436c580d16
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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