2-Fluoro-5-(trifluoromethyl)phenyl isocyanate → HCID 25106932, compound

HRID 1397481Notes

Reaction equation

HRID 1397481 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:12][C:11]([C:13]3([OH:19])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[N:10][CH:9]=2)=[N:6][CH:7]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=1[N:31]=[C:32]=[O:33]>O1CCCC1>[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=1[NH:31][C:32]([NH:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[S:12][C:11]([C:13]3([OH:19])[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[N:10][CH:9]=2)=[CH:4][CH:3]=1)=[O:33]

Participants

4

Reactant 2

HCID 27333802-Fluoro-5-(trifluoromethyl)phenyl isocyanateHCID 68720410HCID 68720410, compound

Product 1

HCID 25106932HCID 25106932, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 7B (0.042 mg, 0.151 mmol) in tetrahydrofuran (1 mL) was added 2-fluoro-5-trifluoromethylphenyl isocyanate (0.022 mL, 0.151 mmol). After 1 h, the mixture was concentrated under reduced pressure. The residue was purified by RP-HPLC (preparative reversed-phase high pressure liquid chromatography) using a Zorbax SB-C18 7M 21.2×250 mm column with UV detection analyzed at 220 and 254 nM (preparative method: water with 0.1% trifluoroacetic acid and CH3CN with 0.1% trifluoroacetic acid gradient 5-95% CH3CN over 30 minutes at 15 mL/min) to provide the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.68 (br d, J=12.9 Hz, 2 H), 2.07-2.17 (m, 2 H), 3.68-3.80 (m, 4 H), 6.15 (s, 1 H), 7.40-7.45 (m, 1 H), 7.52 (m, 1 H), 7.89 (m, 1 H), 8.08 (m, 1 H), 8.25 (s, 1 H), 8.55-8.60 (m, 2 H), 9.10 (s, 1 H), 9.40 (s, 1 H); MS (ESI) m/z 483 [M+H]+.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe residue was purified by RP-HPLC (preparative reversed-phase high pressure liquid chromatography)
  3. customanalyzed at 220 and 254 nM (preparative method: water with 0.1% trifluoroacetic acid and CH3CN with 0.1% trifluoroacetic acid gradient 5-95% CH3CN over 30 minutes at 15 mL/min)

Sources & evidence

ORD record
ord-1eaa2b2b59f24fc18a71332a0dd0e5ed
Source dataset
uspto-grants-2014_12
Patent number
US08901152B2

Reaction notes

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