Diisopropylethylamine → HCID 90410701, compound

HRID 1848717Notes

Reaction equation

HRID 1848717 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17])[O:5][CH2:6][C:7]1[CH:11]=[CH:10][N:9]([CH3:12])[N:8]=1.[F:19][C:20]1[CH:25]=[C:24]([O:26][C:27]([F:30])([F:29])[F:28])[CH:23]=[CH:22][C:21]=1[CH2:31][NH2:32].CCN(C(C)C)C(C)C>C(#N)C>[F:19][C:20]1[CH:25]=[C:24]([O:26][C:27]([F:28])([F:29])[F:30])[CH:23]=[CH:22][C:21]=1[CH2:31][NH:32][C:2]1[CH:3]=[C:4]([O:5][CH2:6][C:7]2[CH:11]=[CH:10][N:9]([CH3:12])[N:8]=2)[CH:13]=[CH:14][C:15]=1[N+:16]([O-:18])=[O:17]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 665234822-Fluoro-4-(trifluoromethoxy)benzenemethanamineHCID 828819703-((3-Fluoro-4-nitrophenoxy)methyl)-1-methyl-1H-pyrazole

Product 1

HCID 90410701HCID 90410701, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-((3-fluoro-4-nitrophenoxy)methyl)-1-methyl-1H-pyrazole (70.0 g, 0.28 mol), (2-fluoro-4-(trifluoromethoxy)phenyl)methanamine (58.3 g, 0.28 mol), DIPEA (63.1 mL, 0.36 mol) and acetonitrile (350 mL) was stirred at 80° Celsius for 16 h. The reaction was cooled to RT, concentrated to dryness, and the resulting residue was recrystallized from ethanol (350 mL) and H2O (350 mL). The solid was collected by filtration and rinsed with a mixture of H2O/ethanol (3:1, 200 mL) followed by hexanes (2×300 mL) yielding the title compound as a yellow solid (116.3 g, 94.7%). MS (ESI): mass calcd. for C19H16F4N4O4, 440.1; m/z found, 441.0 [M+H]+. 1H NMR (600 MHz, CDCl3) δ 8.68-8.52 (m, 1H), 8.20-8.14 (d, J=9.5, 1H), 7.39-7.34 (m, 1H), 7.34-7.31 (d, J=2.2, 1H), 7.06-6.97 (d, J=9.8, 2H), 6.42-6.33 (dd, J=9.5, 2.5, 1H), 6.33-6.24 (m, 2H), 5.09-5.01 (s, 2H), 4.60-4.52 (d, J=5.9, 2H), 3.93-3.85 (s, 3H).

Workup

  1. concentrationconcentrated to dryness
  2. customthe resulting residue was recrystallized from ethanol (350 mL) and H2O (350 mL)
  3. filtrationThe solid was collected by filtration
  4. washrinsed with a mixture of H2O/ethanol (3:1, 200 mL)

Sources & evidence

ORD record
ord-82707aaa084849d788929756b5d12020
Source dataset
uspto-grants-2015_02
Patent number
US08952177B2

Reaction notes

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