Piperidine → HCID 59486023, compound

HRID 1972285Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=3)[CH2:11][N:10]([CH2:23][C:24]3[CH:25]=[N:26][C:27](Cl)=[CH:28][CH:29]=3)[C:9]2=[O:31])=[CH:4][CH:3]=1.[NH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:22])[F:21])[CH:14]=3)[CH2:11][N:10]([CH2:23][C:24]3[CH:25]=[N:26][C:27]([N:32]4[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)=[CH:28][CH:29]=3)[C:9]2=[O:31])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of (S)-3-(4-chlorophenyl)-1-((6-chloropyridin-3-yl)methyl)-4-(3-(trifluoromethyl)phenyl)imidazolidin-2-one (34 mg, 0.073 mmol), piperidine (0.5 mL) and pyridine (2 mL) are heated for 2 days at 130° C. The residue is purified by preparatory LC/MS to provide the title compound; 1H NMR (CD3OD, 400 MHz) δ 7.89 (dd, J=9.6, 6.4 Hz, 1H), 7.75 (d, J=1.6 Hz, 1H), 7.50-7.41 (m, 4H), 7.32-7.27 (m, 3H), 7.15 (d, J=9.2 Hz, 2H), 5.45 (dd, J=9.2, 6.4 Hz, 1H), 4.34 (s, 2H), 3.88 (t, J=9.2 Hz, 1H), 3.60-3.58 (m, 4H), 3.16 (dd, J=9.0, 6.2 Hz, 1H), 1.72-1.61 (m, 6H); HPLC-MS calculated for C27H26ClF3N4O (M+H+) 515.1, found 515.1.

Workup

customThe residue is purified by preparatory LC/MS

Sources & evidence

ORD record: ord-539995e517744fd592477d40ee75249d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431607B2

Reaction notes

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