4-Fluorophenyl isocyanate → HCID 66997474, compound

HRID 2363644Notes

Reaction equation

HRID 2363644 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]1[N:8]=[C:7]([N:9]2[CH2:13][C@@H:12]3[C@@H:14]([NH2:17])[CH2:15][CH2:16][C@@H:11]3[CH2:10]2)[CH:6]=[CH:5][CH:4]=1.[F:20][C:21]1[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[O:29])=[CH:23][CH:22]=1>ClCCl.CCOCC>[F:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:17][C@@H:14]2[C@@H:12]3[C@@H:11]([CH2:10][N:9]([C:7]4[CH:6]=[CH:5][CH:4]=[C:3]([C:2]([F:1])([F:18])[F:19])[N:8]=4)[CH2:13]3)[CH2:16][CH2:15]2)=[O:29])=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 709554-Fluorophenyl isocyanateHCID 66590059(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 66997474HCID 66997474, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine from Example 264 Step A (0.050 g, 0.184 mmol) in dichloromethane (0.1 mL) was added 1-fluoro-4-isocyanatobenzene (0.025 mL, 0.221 mmol). The reaction was stirred at ambient temperature for 30 minutes. The reaction was diluted with ether and sonicated, then filtered and washed with ether to give the title compound: 1H NMR (400 MHz, pyridine-d5) δ ppm 8.45 (s, 1H), 7.63 (dd, J=9.1, 4.9, 2H), 7.46 (t, J=7.9, 1H), 7.00 (t, J=8.8, 2H), 6.93 (d, J=8.8, 1H), 6.51 (d, J=7.7, 1H), 6.21 (d, J=6.7, 1H), 4.27-4.12 (m, 1H), 3.73-3.44 (m, 3H), 3.28 (dd, J=11.0, 4.0, 1H), 2.77-2.57 (m, 2H), 2.12 (td, J=12.7, 6.8, 1H), 1.87 (td, J=13.3, 7.9, 1H), 1.57 (dq, J=12.8, 7.8, 1H), 1.37 (dtd, J=13.2, 7.8, 5.3, 1H); MS (ESI+) m/z 409 (M+H)+.

Workup

  1. customsonicated
  2. filtrationfiltered
  3. washwashed with ether

Sources & evidence

ORD record
ord-e7a8287aa0934037b2c16cd627e8f07c
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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