3-Fluorophenyl isocyanate → HCID 11488008, compound

HRID 239869Notes

Reaction equation

HRID 239869 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[CH:15][C:14]([CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:13]3[C:9]=2[C:10]([NH2:24])=[N:11][NH:12]3)=[CH:4][CH:3]=1.[F:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([N:32]=[C:33]=[O:34])[CH:27]=1>ClCCl>[NH2:24][C:10]1[C:9]2[C:13](=[C:14]([CH2:17][N:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[CH:15]=[CH:16][C:8]=2[C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:33]([NH:32][C:28]3[CH:29]=[CH:30][CH:31]=[C:26]([F:25])[CH:27]=3)=[O:34])=[CH:3][CH:4]=2)[NH:12][N:11]=1

Participants

4

Reactant 2

HCID 1230643-Fluorophenyl isocyanateHCID 16125512HCID 16125512, compound

Product 1

HCID 11488008HCID 11488008, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 15G (50 mg, 0.155 mmol) in dichloromethane was cooled to 0° C., treated with 1-fluoro-3-isocyanatobenzene (0.021 mL), stirred at room temperature overnight, and concentrated. The concentrate was purified by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size) using a gradient of 10% to 100% acetonitrile/0.1% aqueous TFA over 8 minutes (10 minute run time) at a flow rate of 40 mL/min to provide 24 mg of the desired product as the trifluoroacetate salt. 1H NMR (300 MHz, DMSO-d6) δ 3.20-4.20 (m, 8H), 4.56 (s, 2H), 6.79 (m, 1H), 6.92 (d, J=7.12 Hz, 1H), 7.16 (m, 1H), 7.32 (m, 1H), 7.42 (m, 3H), 7.52 (m, 1H), 7.63 (d, J=8.81 Hz, 2H), 9.12 (s, 1H), 9.16 (s, 1H); MS (ESI(+)) m/e 461 (M+H)+.

Workup

  1. concentrationconcentrated
  2. customThe concentrate was purified by preparative HPLC on a Waters Symmetry C8 column (25 mm×100 mm, 7 μm particle size)
  3. customover 8 minutes
  4. custom(10 minute run time)

Sources & evidence

ORD record
ord-dcca2c812f9542cf8460831a435381a1
Source dataset
uspto-grants-2014_02
Patent number
US08642776B2

Reaction notes

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