2,4-Difluorophenyl isocyanate → HCID 11669097, compound

HRID 1626204Notes

Reaction equation

HRID 1626204 reaction equation
[N:1]1([CH2:5][CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:9]=2[C:15]2[N:19]([CH3:20])[N:18]=[CH:17][CH:16]=2)[CH2:4][CH2:3][CH2:2]1.[F:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[N:29]=[C:30]=[O:31]>C(Cl)Cl>[N:1]1([CH2:5][CH2:6][O:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:30]([NH:29][C:23]3[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:22]=3[F:21])=[O:31])=[CH:10][C:9]=2[C:15]2[N:19]([CH3:20])[N:18]=[CH:17][CH:16]=2)[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 5932582,4-Difluorophenyl isocyanateHCID 58964309HCID 58964309, compound

Product 1

HCID 11669097HCID 11669097, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-(azetidin-1-yl)ethoxy)-3-(1-methyl-1H-pyrazol-5-yl)benzenamine (40.1 mg, 0.147 mmol) in CH2Cl2 (2 mL) was added 2,4-difluorophenyl isocyanate (18 μL, 0.152 mmol) and stirred for two hours. The crude reaction mixture was purified by SiO2 column chromatography (Eluent: methanol/CH2Cl2=1/6) to afford the title compound (50.4 mg, 80%). LCMS m/z (%)=428 (MH+, 100), 1H NMR (400 MHz, DMSO-d6) δ: 8.96 (bs, 1H), 8.47 (bs, 1H), 8.09-7.98 (m, 1H), 7.45-7.39 (m, 2H), 7.36 (d, J=2.71 Hz, 1H), 7.34-7.26 (m, 1H), 7.06 (d, J=8.94 Hz, 1H), 7.06-6.98 (m, 1H), 6.23 (d, J=1.85 Hz, 1H), 3.89 (t, J=5.49 Hz, 2H), 3.67 (s, 3H), 2.98 (t, J=6.92 Hz, 4H), 2.60 (t, J=5.47 Hz, 2H), 1.86 (quintet, J=6.99 Hz, 2H).

Workup

  1. customThe crude reaction mixture
  2. customwas purified by SiO2 column chromatography (Eluent: methanol/CH2Cl2=1/6)

Sources & evidence

ORD record
ord-21001cd1357d410da80cded506b738a3
Source dataset
uspto-grants-2014_07
Patent number
US08785441B2

Reaction notes

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