(6-Methylpyridin-2-yl)thiourea → N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-fluorothiazol-2-yl)-6-methylpyridin-2-amine

HRID 1520205Notes

Reaction equation

HRID 1520205 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13](=O)[CH:14](Br)[F:15])[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[CH3:20][C:21]1[N:26]=[C:25]([NH:27][C:28]([NH2:30])=[S:29])[CH:24]=[CH:23][CH:22]=1>CC(C)=O>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]3[N:30]=[C:28]([NH:27][C:25]4[CH:24]=[CH:23][CH:22]=[C:21]([CH3:20])[N:26]=4)[S:29][C:14]=3[F:15])[CH:10]=[N:9]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 685983(6-Methylpyridin-2-yl)thioureaHCID 866585601-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-bromo-2-fluoroethanone

Product 1

HCID 86658559N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-fluorothiazol-2-yl)-6-methylpyridin-2-amineYield 92.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

According to Scheme 6 Step 3: A solution of 1-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-2-bromo-2-fluoroethanone (0.26 mmol, 110 mg) and of 1-(6-methylpyridin-2-yl)thiourea (0.26 mmol, 44 mg) in acetone (3 mL) was stirred at 50° C. for 5 hours. A precipitate was formed, was filtered and was washed with Et2O to yield N-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-fluorothiazol-2-yl)-6-methylpyridin-2-amine (0.24 mmol, 95 mg, 92%) as a beige solid.

Workup

  1. customA precipitate was formed
  2. filtrationwas filtered
  3. washwas washed with Et2O

Sources & evidence

ORD record
ord-a6f5f4b70e56446ca6d55a4ae28b468f
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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