Sodium hydride → HCID 67500393, compound

HRID 1428355Notes

Reaction equation

HRID 1428355 reaction equation
[Cl:1][C:2]1[C:6]([NH:7][C:8]([NH:10][CH2:11][CH2:12]Cl)=[O:9])=[CH:5][N:4]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[N:3]=1.[H-].[Na+]>C1COCC1>[Cl:1][C:2]1[C:6]([N:7]2[CH2:12][CH2:11][NH:10][C:8]2=[O:9])=[CH:5][N:4]([C:14]2[CH:15]=[N:16][CH:17]=[CH:18][CH:19]=2)[N:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 67499852HCID 67499852, compound

Product 1

HCID 67500393HCID 67500393, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-3-(2-chloroethyl)urea (0.1 g, 0.333 mmol) in THF (6.66 ml) was added sodium hydride (8.00 mg, 0.333 mmol) and the reaction mixture was stirred at ambient temperature for 30 minutes. The reaction was quenched by the addition of a solution of saturated ammonium chloride and the product was extracted with ethyl acetate (2×). The combined organic layers were dried over sodium sulfate, filtered and concentrated. The product was a beige solid which was pure and did not need any further purification (63 mg, 72%): mp 167-170° C.; 1H NMR (400 MHz, CDCl3) δ 8.96 (d, J=2.2 Hz, 1H), 8.56 (dd, J=4.7, 1.4 Hz, 1H), 8.33 (s, 1H), 7.99 (ddd, J=8.3, 2.7, 1.4 Hz, 1H), 7.40 (ddd, J=8.3, 4.8, 0.7 Hz, 1H), 5.00 (s, 1H), 4.14-4.07 (m, 2H), 3.68-3.58 (m, 2H); ESIMS m/z 264 ([M+H]+).

Workup

  1. customThe reaction was quenched by the addition of a solution of saturated ammonium chloride
  2. extractionthe product was extracted with ethyl acetate (2×)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customany further purification (63 mg, 72%)

Sources & evidence

ORD record
ord-7bc967030e8d43599f6ae9daf186a686
Source dataset
uspto-grants-2015_01
Patent number
US08937083B2

Reaction notes

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