4-Fluorophenyl isocyanate → 1-[3-(4-Fluoro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(4-fluoro-phenyl)-urea

HRID 919463Notes

Reaction equation

HRID 919463 reaction equation
[F:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH2:16])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15].[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[O:26])=[CH:20][CH:19]=1>C(Cl)Cl>[F:1][C:2]1[CH:6]=[N:5][N:4]([CH3:7])[C:3]=1[C:8]1[CH:9]=[C:10]([NH:16][C:25]([NH:24][C:21]2[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=2)=[O:26])[CH:11]=[CH:12][C:13]=1[O:14][CH3:15]

Participants

4

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 231394493-(4-fluoro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine

Product 1

HCID 116246391-[3-(4-Fluoro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenyl]-3-(4-fluoro-phenyl)-ureaYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-Fluoro-2-methyl-2H-pyrazol-3-yl)-4-methoxy-phenylamine (45 mg, 0.20 mmol) was dissolved in 3 mL of CH2Cl2, treated with 4-fluorophenylisocyanate (28 μL, 0.24 mmol), and stirred at room temperature overnight. The compound of interest precipitated out of solution and was filtered and washed with CH2Cl2 to afford Compound 31 as a white solid, 56 mg, 77% yield: LCMS m/z (%)=359 (M+H, 100). 1H NMR (400 MHz, acetone-d6) δ: 8.12 (s, 1H), 8.08 (s, 1H), 7.63 (ddd, J1=9.0 Hz, J2=2.6 Hz, 1H), 7.54 (m, 2H), 7.48 (d, J=2.8 Hz, 1H), 7.38 (d, JH,F=4.8 Hz, 1H), 7.13 (d, J=8.8 Hz, 1H), 7.05 (dd, J1=9.0 Hz, J2=9.0 Hz, 2H), 3.83 (s, 3H), 3.65 (s, 3H). 19F NMR (376 MHz, acetone-d6) δ: −123.08 (m, 1F), −177.41 (d, JH,F=5.3 Hz, 1F).

Workup

  1. customThe compound of interest precipitated out of solution
  2. filtrationwas filtered
  3. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-6afe6598c3de42f0b59a3242ccc5aae1
Source dataset
uspto-grants-2016_03
Patent number
US09273035B2

Reaction notes

Loading…