Sodium hydride → HCID 86681071, compound

HRID 1848091Notes

Reaction equation

HRID 1848091 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:8](=[O:13])[NH:9][CH:10]=[CH:11][N:12]=2)[CH:4]=[N:3]1.[H-].[Na+].Cl[CH2:17][C:18]1[CH:28]=[CH:27][C:21]2[N:22]=[C:23]([S:25][CH3:26])[S:24][C:20]=2[CH:19]=1>CN(C=O)C>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[C:8](=[O:13])[N:9]([CH2:17][C:18]3[CH:28]=[CH:27][C:21]4[N:22]=[C:23]([S:25][CH3:26])[S:24][C:20]=4[CH:19]=3)[CH:10]=[CH:11][N:12]=2)[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 866809946-(Chloromethyl)-2-(methylthio)benzo[d]thiazoleHCID 86681070HCID 86681070, compound

Product 1

HCID 86681071HCID 86681071, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-(1-methyl-1H-pyrazol-4-yl)pyrazin-2(1H)-one (139 mg, 0.78 mmol) from Step 2 of this Example in DMF (3 mL) was added NaH (60% in mineral oil, 32 mg, 0.78 mmol) and the mixture was stirred at rt for 10 min. 6-(Chloromethyl)-2-(methylthio)benzo[d]thiazole (180 mg, 0.78 mmol) from Step 4 of Example 36 was then added. The mixture was stirred at rt overnight and then concentrated under reduced pressure. The residue was purified by silica gel chromatography eluting with 0-15% MeOH/DCM to afford impure 3-(1-methyl-1H-pyrazol-4-yl)-1-((2-(methylthio)benzo[d]thiazol-6-yl)methyl)pyrazin-2(1H)-one (80 mg, 27%) which was used without further purification. LCMS (ESI) m/z 370 (M+H)+.

Workup

  1. stirringThe mixture was stirred at rt overnight
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography
  4. washeluting with 0-15% MeOH/DCM

Sources & evidence

ORD record
ord-d9233fe4c4094bcf93ace1371bc94286
Source dataset
uspto-grants-2015_02
Patent number
US08952058B2

Reaction notes

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