Diisopropylethylamine → 1-(3-acetyl-phenyl)-3-[5-trifluoromethyl-2-(2-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-urea

HRID 1673009Notes

Reaction equation

HRID 1673009 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([NH2:18])[N:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]([F:17])([F:16])[F:15])[N:7]=1.CCN(C(C)C)C(C)C.[N:30]([C:33]1[CH:34]=[C:35]([C:39](=[O:41])[CH3:40])[CH:36]=[CH:37][CH:38]=1)=[C:31]=[O:32]>C(Cl)Cl>[C:39]([C:35]1[CH:34]=[C:33]([NH:30][C:31]([NH:18][C:5]2[N:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:14]([F:16])([F:17])[F:15])[N:7]=[C:3]([C:2]([F:1])([F:19])[F:20])[CH:4]=2)=[O:32])[CH:38]=[CH:37][CH:36]=1)(=[O:41])[CH3:40]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 3127181-(3-Isocyanatophenyl)ethan-1-oneHCID 592402835-trifluoromethyl-2-(2-trifluoromethylphenyl)-2H-pyrazol-3-ylamine

Product 1

HCID 592401821-(3-acetyl-phenyl)-3-[5-trifluoromethyl-2-(2-trifluoromethyl-phenyl)-2H-pyrazol-3-yl]-ureaYield 26.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-trifluoromethyl-2-(2-trifluoromethyl-phenyl)-2H-pyrazol-3-ylamine (97 mg, 0.33 mmol) and DIEA (57 μL, 0.33 mmol) in DCM (2 mL) was added 3′-isocyanato-acetophenone (41 μL, 0.30 mmol). After 15 h the reaction mixture was concentrated and purified by chromatography (silica, EtOAc/Hex, 0:100 to 50:50) to yield the title compound (36 mg). 1H-NMR (DMSO-d6): δ 9.67 (1H, s), 8.24 (1H, m), 7.99 (1H, d), 7.94-7.80 (3H, m), 7.69 (1H, d), 7.62 (1H, d), 7.48 (1H, t), 6.31 (2H, s), 2.57 (3H, s); MS (ES): 457 [M+H]+.

Workup

  1. concentrationAfter 15 h the reaction mixture was concentrated
  2. custompurified by chromatography (silica, EtOAc/Hex, 0:100 to 50:50)

Sources & evidence

ORD record
ord-e2070ce9b5cf4dd295f6f0f8a0e9bea3
Source dataset
uspto-grants-2011_08
Patent number
US07998995B2

Reaction notes

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