Sodium hydride → HCID 57422490, compound

HRID 658747Notes

Reaction equation

HRID 658747 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-6649b7ae3f954462b4e3a59895a57f42
Source dataset
uspto-grants-2011_12
Patent number
US08076491B2

Reaction notes

Loading…