2-Fluorophenyl isocyanate → HCID 11517754, compound

HRID 1626211Notes

Reaction equation

HRID 1626211 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH2:22])[CH:10]=[CH:11][C:12]=2[O:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:5][CH:4]=[N:3]1.[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[N:30]=[C:31]=[O:32]>C(Cl)Cl>[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[NH:30][C:31]([NH:22][C:9]1[CH:10]=[CH:11][C:12]([O:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:7]([C:6]2[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=2)[CH:8]=1)=[O:32]

Participants

4

Reactant 2

HCID 855882-Fluorophenyl isocyanateHCID 58964257HCID 58964257, compound

Product 1

HCID 11517754HCID 11517754, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(2-Methyl-2H-pyrazol-3-yl)-4-(2-piperidin-1-yl-ethoxy)-phenylamine (21.0 mg, 0.07 mmol) in methylene chloride (1 mL) was treated with 2-fluorophenyl isocyanate (0.074 mmol), then the reaction mixture stirred at room temperature overnight and concentrated to give an oily residue that was subjected to a purification by flash chromatography (SiO2, CH2Cl2/MeOH gradient elution) to afford Compound 65 as a white solid in 45.1% yield. LCMS m/z (%)=438.4 (M+H, 100). 1H NMR (400 MHz, DMSO-d6) δ: 8.52 (bs, 1H), 8.32-8.28 (m, 1H), 8.02 (bs, 1H), 7.57 (dd, J=2.7, 8.9 Hz, 1H), 7.48 (d, J=2.7 Hz, 1H), 7.39 (d, J=1.8 Hz, 1H), 7.18-7.06 (m, 3H), 7.00-6.92 (m, 1H), 6.22 (d, J=1.8 Hz, 1H), 4.11-4.08 (m, 2H), 3.75 (s, 3H), 2.67-2.60 (m, 2H), 2.42-2.31 (m, 4H), 1.52-1.43 (m, 4H), 1.40-1.32 (m, 2H).

Workup

  1. concentrationconcentrated
  2. customto give an oily residue that
  3. customwas subjected to a purification by flash chromatography (SiO2, CH2Cl2/MeOH gradient elution)

Sources & evidence

ORD record
ord-dee8a52b13f74c9bbde9608721bfc088
Source dataset
uspto-grants-2014_07
Patent number
US08785441B2

Reaction notes

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