4-Fluorophenyl isocyanate → HCID 66997447, compound

HRID 2363663Notes

Reaction equation

HRID 2363663 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:19]=[CH:18][C:17]([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:16][CH:15]=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:17]3[CH:16]=[CH:15][C:14]([O:13][C:12]([F:11])([F:29])[F:30])=[CH:19][CH:18]=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 66997100HCID 66997100, compound

Product 1

HCID 66997447HCID 66997447, compound

Procedure

The title compound was prepared by substituting 2-isocyanato-2-methylpropane for 1-fluoro-4-isocyanatobenzene and (3aR,4S,6aS)-2-(4-(trifluoromethoxy)phenyl)octahydrocyclopenta[c]pyrrol-4-amine from Example 716 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 7.19 (d, J=9.0 Hz, 2H), 6.61-6.51 (m, 2H), 6.26 (d, J=7.1 Hz, 1H), 5.89 (s, 1H), 4.30-4.18 (m, 1H), 3.51 (dd, J=9.8, 3.2 Hz, 1H), 3.24 (dd, J=9.7, 7.8 Hz, 1H), 3.10 (dd, J=9.4, 7.8 Hz, 1H), 2.95 (dd, J=9.6, 3.5 Hz, 1H), 2.71-2.54 (m, 2H), 2.11-2.00 (m, 1H), 1.93-1.79 (m, 1H), 1.56-1.49 (m, 1H), 1.47 (s, 9H), 1.40-1.23 (m, 1H); MS (ESI+) m/z 386 (M+H)+.

Sources & evidence

ORD record
ord-977d1742635d4718baa4751fa8dde1b4
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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