4-Chlorophenyl Isocyanate → HCID 11539116, compound

HRID 540585Notes

Reaction equation

HRID 540585 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[C:10]1[N:11]([CH3:19])[N:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1>C(Cl)Cl>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([C:10]3[N:11]([CH3:19])[N:12]=[C:13]([C:15]([F:18])([F:16])[F:17])[CH:14]=3)[CH:5]=2)=[O:29])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 23139425HCID 23139425, compound

Product 1

HCID 11539116HCID 11539116, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methoxy-3-(2-methyl-5-trifluoromethyl-2H-pyrazol-3-yl)-phenylamine (0.02 g, 0.08 mmol) was treated with 4-chlorophenyl isocyanate (0.01 g, 10.45 μL, 0.093 mmol, 1.2 equiv.) in CH2Cl2 (3.0 mL), in a similar manner as described in Example 1.102. The product was further purified via reverse phase C-18 HPLC to afford Compound 42 (0.03 g, 0.07 mmol, 88% yield) as a white solid: LCMS m/z (%)=425 (M+H37Cl, 100), 427 (M+H35Cl, 34). 1H NMR (400 MHz, MeOH-d4) δ: 7.50 (dd, J=10.0, 2.0 Hz, 1H), 7.42 (dd, J=8.0 Hz, 3H), 7.27 (dd, J=6.0, 2.0 Hz, 2H), 7.12 (d, J=8.0 Hz, 1H), 3.84 (s, 3H), 3.76 (s, 3H).

Workup

  1. customThe product was further purified via reverse phase C-18 HPLC

Sources & evidence

ORD record
ord-ed7c0d48dcdb4a6da0e7fada10066c78
Source dataset
uspto-grants-2014_10
Patent number
US08871797B2

Reaction notes

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