4-Fluorophenyl isocyanate → HCID 66996875, compound

HRID 2363664Notes

Reaction equation

HRID 2363664 reaction equation
FC1C=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4]C=1.[F:11][C:12]([F:30])([F:29])[O:13][C:14]1[CH:15]=[C:16]([N:20]2[CH2:24][C@@H:23]3[C@@H:25]([NH2:28])[CH2:26][CH2:27][C@@H:22]3[CH2:21]2)[CH:17]=[CH:18][CH:19]=1.F[C:32](F)(F)C1N=C(N2C[C@@H]3[C@@H](N)CC[C@@H]3C2)C=CC=1>>[C:5]([NH:8][C:9]([NH:28][C@@H:25]1[C@@H:23]2[C@@H:22]([CH2:21][N:20]([C:16]3[CH:17]=[CH:18][CH:19]=[C:14]([O:13][C:12]([F:11])([F:29])[F:30])[CH:15]=3)[CH2:24]2)[CH2:27][CH2:26]1)=[O:10])([CH3:32])([CH3:6])[CH3:4]

Participants

4

Reactant 3

HCID 709554-Fluorophenyl isocyanateHCID 66590059(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amineHCID 66996732HCID 66996732, compound

Product 1

HCID 66996875HCID 66996875, compound

Procedure

The title compound was prepared by substituting 2-isocyanato-2-methylpropane for 1-fluoro-4-isocyanatobenzene and (3aR,4S,6aS)-2-(3-(trifluoromethoxy)phenyl)octahydrocyclopenta[c]pyrrol-4-amine from Example 715 Step 1 for (3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine in the procedure described in Example 709: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.24 (d, J=8.2 Hz, 1H), 6.68 (dd, J=8.1, 0.9 Hz, 1H), 6.57-6.47 (m, 2H), 6.25 (d, J=7.1 Hz, 1H), 5.89 (s, 1H), 4.26-4.18 (m, 1H), 3.49 (dd, J=9.9, 3.2 Hz, 1H), 3.27 (dd, J=9.8, 7.8 Hz, 1H), 3.12 (dd, J=9.6, 7.8 Hz, 1H), 2.94 (dd, J=9.7, 3.4 Hz, 1H), 2.68-2.56 (m, 2H), 2.06 (td, J=12.6, 6.4 Hz, 1H), 1.85 (td, J=13.2, 7.7 Hz, 1H), 1.56-1.49 (m, 1H), 1.47 (s, 9H), 1.35-1.26 (m, 1H); MS (ESI+) m/z 386 (M+H)+.

Sources & evidence

ORD record
ord-c09bdf38d1114bf59dc40c0fcc327b7b
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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