Triethylamine → HCID 54674495, compound

HRID 2402747Notes

Reaction equation

[CH2:1]1[C@H:5]2[CH2:6][CH2:7][C@@H:8]([OH:9])[C@H:4]2[CH2:3][NH:2]1.Br[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[N:12]=1.C(N(CC)CC)C>C(O)C>[F:18][C:17]([F:20])([F:19])[C:13]1[N:12]=[C:11]([N:2]2[CH2:3][C@@H:4]3[C@H:8]([OH:9])[CH2:7][CH2:6][C@@H:5]3[CH2:1]2)[CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 80 °C

Procedure

(3aR,4R,6aS)-Octahydrocyclopenta[c]pyrrol-4-ol (1.65 g, 12.97 mmol) from Example 29, 2-bromo-6-(trifluoromethyl)pyridine (3.66 g, 16.22 mmol) and triethylamine (7.23 mL, 51.9 mmol) were combined in ethanol (7.23 mL). The reaction was heated at 80° C. for 24 hours and the solvent was concentrated in vacuo. The resulting residue was purified by silica gel chromatography using 0-40% ethyl acetate/hexane as eluent to give the title compound and the title compound of Example 31: 1H NMR (500 MHz, pyridine-d5) δ ppm 7.47 (t, J=7.9, 1H), 6.94 (d, J=7.2, 1H), 6.53 (d, J=8.6, 1H), 6.38 (d, J=4.1, 1H), 4.47-4.38 (m, 1H), 4.12 (dd, J=11.0, 4.3, 1H), 3.70-3.63 (m, 1H), 3.53 (t, J=10.0, 1H), 3.38 (dd, J=10.4, 4.6, 1H), 2.80-2.73 (m, 1H), 2.72-2.64 (m, 1H), 1.97-1.74 (m, 3H), 1.64-1.56 (m, 1H); MS (ESI+) m/z 273 (M+H)+.

Workup

concentrationthe solvent was concentrated in vacuo
customThe resulting residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-de584e01ab76463c8a850ea88cc7ab16
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796470B2

Reaction notes

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