2-Chloroethyl isocyanate → HCID 57422492, compound

HRID 548181Notes

Reaction equation

HRID 548181 reaction equation
[CH3:1][C:2]1[C:6]([CH2:7][N:8]2[CH:12]=[C:11]([NH2:13])[CH:10]=[N:9]2)=[C:5]([CH3:14])[O:4][N:3]=1.[Cl:15][CH2:16][CH2:17][N:18]=[C:19]=[O:20]>C(#N)C>[Cl:15][CH2:16][CH2:17][NH:18][C:19]([NH:13][C:11]1[CH:10]=[N:9][N:8]([CH2:7][C:6]2[C:2]([CH3:1])=[N:3][O:4][C:5]=2[CH3:14])[CH:12]=1)=[O:20]

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 337812431-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-amine

Product 1

HCID 57422492HCID 57422492, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-((3,5-dimethylisoxazol-4-yl)methyl)-1H-pyrazol-4-amine (419 mg, 2.18 mmol) and 2-chloroethyl isocyanate (230 mg, 2.18 mmol) in acetonitrile (5 mL) were heated at 65° C. for 16 hours. The reaction was cooled to room temperature and concentrated on the rotovap. The residue was purified by silica column chromotography (100% to 90% dichloromethane in methanol: 30 minute gradient), dried and triturated with ethyl acetate/hexanes (1/9) to afford (1-(2-chloroethyl)-3-(1-((3,5-dimethylisoxazol-4-yl)methyl)1H-pyrazol-4-yl)urea (258 mg, 40%) as a yellow solid. MS M+H calculated 298.10; found 298.1.

Workup

  1. concentrationconcentrated on the rotovap
  2. customThe residue was purified by silica column chromotography (100% to 90% dichloromethane in methanol: 30 minute gradient)
  3. customdried
  4. customtriturated with ethyl acetate/hexanes (1/9)

Sources & evidence

ORD record
ord-451b5a85135e4a6ebb4ab3f966fc5324
Source dataset
uspto-grants-2011_05
Patent number
US07939671B2

Reaction notes

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