Water → HCID 86658575, compound

HRID 1520223Notes

Reaction equation

HRID 1520223 reaction equation
[CH2:1]([O:3][C:4](=[O:7])[CH2:5]Br)[CH3:2].[CH3:8][C:9]1[S:13][C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[N:11][C:10]=1[C:21]1[CH:22]=[N:23][NH:24][CH:25]=1.C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[CH3:8][C:9]1[S:13][C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[N:11][C:10]=1[C:21]1[CH:22]=[N:23][N:24]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:7])[CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 25138329HCID 25138329, compound

Product 1

HCID 86658575HCID 86658575, compoundYield 32.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

According to Scheme 18 Step 1: Ethyl-2-bromoacetate (0.27 mmol, 45.4 mg) was added to a suspension of N-(5-methyl-4-(1H-pyrazol-4-yl)thiazol-2-yl)pyridin-2-amine (0.27 mmol, 70 mg) and K2CO3 (0.54 mmol, 82 mg) in DMSO (4 mL) and then the reaction mixture was heated at 70° C. for 3 hours. Water was added and the aqueous phase was extracted with AcOEt. The organic phase was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel using cyclohexane/AcOEt (90:10 to 30:70) as eluent to afford ethyl 2-(4-(5-methyl-2-(pyridin-2-ylamino)thiazol-4-yl)-1H-pyrazol-1-yl)acetate (87 μmol, 30 mg, 32%) as a white powder.

Workup

  1. extractionthe aqueous phase was extracted with AcOEt
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationwas filtered
  4. concentrationwas concentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-5eeb2169a77d425c802e04cb6fe963bd
Source dataset
uspto-grants-2015_07
Patent number
US09073907B2

Reaction notes

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