Thiourea → HCID 86665176, compound

HRID 1893724Notes

Reaction equation

HRID 1893724 reaction equation
Br[CH:2]([C:5]([C:7]1[CH:8]=[N:9][N:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH:11]=1)=O)[C:3]#[N:4].[NH2:21][C:22]([NH2:24])=[S:23]>CCO>[NH2:24][C:22]1[S:23][C:2]([C:3]#[N:4])=[C:5]([C:7]2[CH:8]=[N:9][N:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH:11]=2)[N:21]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 86665177HCID 86665177, compound

Product 1

HCID 86665176HCID 86665176, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

According to Scheme 7, Step 3: To a solution of 2-bromo-3-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-3-oxopropanenitrile (25.3 mmol, 8.44 g) in EtOH (120 mL) was added thiourea (26.5 mmol, 2.06 g). The resulting mixture was stirred at reflux for 2 hours. After cooling to room temperature, the solvent was removed under reduced pressure. The residue was purified by silica column on combi-flash EtOAc/PE (1:10 to ˜1:1) to give 2-amino-4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazole-5-carbonitrile as a yellow solid (22.0 mmol, 6.83 g, 87%).

Workup

  1. temperatureat reflux for 2 hours
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified by silica column on combi-flash EtOAc/PE (1:10 to ˜1:1)

Sources & evidence

ORD record
ord-f5e8efc18bfb41f082d99cf5148684d0
Source dataset
uspto-grants-2013_08
Patent number
US08513252B2

Reaction notes

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