HCID 66668605, compound → HCID 66889224, compound

HRID 1893725Notes

Reaction equation

HRID 1893725 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[OH:7].Br[C:9]1[S:10][C:11]([C:28]#[N:29])=[C:12]([C:14]2[CH:15]=[N:16][N:17]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[CH:18]=2)[N:13]=1>O1CCOCC1>[CH3:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][N:17]2[CH:18]=[C:14]([C:12]3[N:13]=[C:9]([O:7][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[S:10][C:11]=3[C:28]#[N:29])[CH:15]=[N:16]2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 66668605HCID 66668605, compoundHCID 178516071HCID 178516071, compound

Product 1

HCID 66889224HCID 66889224, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

According to Scheme 7, Step 5: To the reaction mixture of pyridin-2-ol (1.05 mmol, 100 mg) and 2-bromo-4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazole-5-carbonitrile (1.16 mmol, 434 mg) in dioxane (8 mL) was added Ag2O (3.16 mmol, 733 mg). The resulting mixture was stirred at reflux overnight. After cooling to room temperature, the mixture was filtered and concentrated under reduced pressure. The residue was purified by preparative TLC PE/EtOAc (1:1) to give 4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-(pyridin-2-yloxy)thiazole-5-carbonitrile (0.26 mmol, 153 mg, 37%) as a white solid.

Workup

  1. temperatureat reflux overnight
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by preparative TLC PE/EtOAc (1:1)

Sources & evidence

ORD record
ord-c6c915fb89ec484d8f63169a808d55d3
Source dataset
uspto-grants-2013_08
Patent number
US08513252B2

Reaction notes

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