1-(4-Chlorophenyl)ethylamine → HCID 44393171, compound

HRID 986919Notes

Reaction equation

[C:1]1([C@@H:7]([NH:9][C:10]2[CH:15]=[C:14](Cl)[N:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC1C=CC(C(N)C)=CC=1.[F:27][C:28]1[CH:37]=[CH:36][C:31]([O:32][CH2:33][CH2:34][NH2:35])=[CH:30][CH:29]=1>C(Cl)Cl>[F:27][C:28]1[CH:37]=[CH:36][C:31]([O:32][CH2:33][CH2:34][NH:35][C:14]2[CH:15]=[C:10]([NH:9][C@H:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH3:8])[N:11]=[CH:12][N:13]=2)=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 150 °C

Procedure

4-[(1S)-(1-phenylethyl)amino]-6-chloropyrimidine, (Intermediate III, Compound of Example 6), (234 mg, 1.0 mmole) and [2-(4-fluorophenoxy)ethyl]amine (357 mg, 2.3 mmole) were combined in a 2 mL pressure vial which was then securely capped. The vial was heated at 150° C. for 20 hours. After cooling, the solid mass was dissolved in CH2Cl2 (25 mL) and extracted with saturated sodium carbonate (25 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from CH2Cl2 (5 mL) to afford the titled compound as a white solid (191 mg, 54%). 1H NMR (CDCl3) δ 1.54 (d, J=6.6 Hz, 3H), 3.54 (q, J=5.5 Hz, 2H), 3.94 (t, J=5.5 Hz, 2H), 4.59 (p, J=6.6 Hz, 1H), 5.05 (broad m, 1H), 5.08 (s, 1H), 5.34 (broad d,1H), 6.77 (m, 2H), 6.95 (t, J=9.1 Hz, 2H), 7.23 (m,1H), 7.32 (d, J=4.4 Hz, 4H), 8.09 (s, 1H), LC/MS (MH+) m/e 353.79 obs.

Workup

customwas then securely capped
temperatureAfter cooling
extractionextracted with saturated sodium carbonate (25 mL)
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was recrystallized from CH2Cl2 (5 mL)

Sources & evidence

ORD record: ord-0d2131bd6319402d9a73650d15f5141e
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06630469B2

Reaction notes

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