Hydrogen Sulfide → HCID 86071503, compound

HRID 1436878Notes

Reaction equation

[C:1]([C:3]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[C:5](=[O:17])[CH2:4]1)#[N:2].C(N(CC)CC)C.[SH2:31]>N1C=CC=CC=1>[F:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][N:6]2[CH2:7][CH2:8][C:3]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)([C:1](=[S:31])[NH2:2])[CH2:4][C:5]2=[O:17])=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled (0° C.) solution of 4-cyano-1-(4-fluorobenzyl)-4-phenylpiperidin-2-one (3.39 g, 10.9 mmol) in pyridine (77 mL) was added triethylamine (45.0 g, 0.77 mol). The reaction mixture was saturated with hydrogen sulfide gas, the reaction vessel was sealed and then brought to ambient temperature. After stirring for 24 hours, the reaction mixture was cooled (0° C.), the reaction vessel was opened, then the solvents were concentrated under vacuum. The residual material was purified using silica gel column chromatography eluting with 0-70% EtOAc in hexanes. The appropriate fractions were combined and concentrated to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 9.65 (s, 1H), 8.68 (s, 1H), 7.35 (m, 4H), 7.26 (t, J=7 Hz, 1H), 7.13 (t, J=8.3 Hz, 2H), 7.04 (t, J=8.9 Hz, 2H), 4.48 (d, J=15 Hz, 1H), 4.35 (d, J=15 Hz, 1H), 3.16 (m, 2H), 3.93 (d, J=17 Hz, 1H), 2.82 (m, 1H), 2.51 (m, 2H) ppm. ES MS M+1=343.

Workup

customthe reaction vessel was sealed
custombrought to ambient temperature
concentrationthe solvents were concentrated under vacuum
customThe residual material was purified
washeluting with 0-70% EtOAc in hexanes
concentrationconcentrated

Sources & evidence

ORD record: ord-a3b9af6b630048a0b8c92e191f53ee3d
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07619086B2

Reaction notes

Loading…