Water → HCID 178521752, compound

HRID 1696582Notes

Reaction equation

HRID 1696582 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:17])OCC(Cl)(Cl)Cl.[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[CH:29]=[C:28]([NH2:30])[NH:27][N:26]=1.O>CN(C=O)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]([NH:30][C:28]1[NH:27][N:26]=[C:25]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[F:18])[CH:29]=1)=[O:17]

Participants

5

Reactant 3

HCID 962WaterHCID 67272012HCID 67272012, compoundHCID 178507277HCID 178507277, compound

Product 1

HCID 178521752HCID 178521752, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,2,2-trichloroethyl 2,3-dichlorophenylcarbamate (0.286 g, 0.847 mmol; general method D), 3-(2-fluorophenyl)-1H-pyrazol-5-amine (0.150 g, 0.847 mmol) and I-PR2NET (0.219 g, 1.69 mmol) in DMF (1 mL) was stirred at 90° C. overnight. Water was added (30 mL) and the mixture was extracted with EtOAc (3×30 mL), dried (MgSO4), filtered and concentrated to yield crude 1-(2,3-dichlorophenyl)-3-(3-(2-fluorophenyl)-1H-pyrazol-5-yl)urea as an off-white solid (285 mg, 92% yield). 1H-NMR (DMSO-d6): δ 9.86 (s, 1H), 8.25 (d, 1H, J=7.2 Hz), 7.81 (t, 1H, J=7.2 Hz), 7.45-7.27 (m, 5H), 6.65 (s, br, 1H). 5.67 (s, 1H), one urea proton not visible. LC-MS (EI) m/z: 365.0 367.0 (M+H+).

Workup

  1. extractionthe mixture was extracted with EtOAc (3×30 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-cb47fd50c4fb48088b7af49571c8b7aa
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

Loading…