Sodium hydride → HCID 57422490, compound

HRID 1686358Notes

Reaction equation

HRID 1686358 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]([NH:7][C:8]1[CH:9]=[N:10][N:11]([CH2:13][C:14]2[C:15]([CH3:20])=[N:16][O:17][C:18]=2[CH3:19])[CH:12]=1)=[O:6].[H-].[Na+]>CN(C=O)C>[CH3:20][C:15]1[C:14]([CH2:13][N:11]2[CH:12]=[C:8]([N:7]3[CH2:2][CH2:3][NH:4][C:5]3=[O:6])[CH:9]=[N:10]2)=[C:18]([CH3:19])[O:17][N:16]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 57422492HCID 57422492, compound

Product 1

HCID 57422490HCID 57422490, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2-chloroethyl)-3-(1-((3,5-dimethylisoxazol-4-yl)methyl)1H-pyrazol-4-yl)urea (example 10-88b) (115 mg, 0.39 mmol) and 60% sodium hydride (17 mg, 0.42 mmol) in DMF (2 mL) were stirred at 0° C. for 15 minutes then allowed to warm up to room temperature with stirring for 2 hours. The reaction was quenched with methanol and concentrated on the rotovap. The reaction was diluted with brine (50 mL) and extracted with dichloromethane (2×, 50 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated on the rotovap. The residue was purified by silica column chromotography (100% to 90% dichloromethane in methanol:30 minute gradient) to afford 1-(1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-yl)imidazolidin-2-one (98 mg, 97%) as a white solid. 1H NMR (DMSO-d6, 400 MHz): δ2.10 (s, 3H), 2.37 (s, 3H), 3.35-3.39 (m, 2H), 3.61 (d, J=8.8 Hz, 1H), 3.63 (d, J=10.4 Hz, 1H), 5.07 (s, 2H), 6.71 (s, 1H), 7.42 (s, 1H), 7.74 (s, 1H). MS M+H calculated 262.12. found 262.1.

Workup

  1. customThe reaction was quenched with methanol
  2. concentrationconcentrated on the rotovap
  3. additionThe reaction was diluted with brine (50 mL)
  4. extractionextracted with dichloromethane (2×, 50 mL)
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated on the rotovap
  8. customThe residue was purified by silica column chromotography (100% to 90% dichloromethane in methanol:30 minute gradient)

Sources & evidence

ORD record
ord-963a0d973e8940cfac48be0e18f954e1
Source dataset
uspto-grants-2012_04
Patent number
US08148544B2

Reaction notes

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