2-Chloro-8-fluoroquinoline → HCID 72714757, compound

HRID 2364575Notes

Reaction equation

HRID 2364575 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([F:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.Cl.Cl.Cl.[F:16][C:17]1[CH:26]=[C:25]([C:27]2[C:32]([CH:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)=[N:31][CH:30]=[CH:29][N:28]=2)[CH:24]=[CH:23][C:18]=1[C:19]([NH:21][CH3:22])=[O:20]>>[F:16][C:17]1[CH:26]=[C:25]([C:27]2[C:32]([CH:33]3[CH2:38][CH2:37][N:36]([C:2]4[CH:11]=[CH:10][C:9]5[C:4](=[C:5]([F:12])[CH:6]=[CH:7][CH:8]=5)[N:3]=4)[CH2:35][CH2:34]3)=[N:31][CH:30]=[CH:29][N:28]=2)[CH:24]=[CH:23][C:18]=1[C:19]([NH:21][CH3:22])=[O:20]

Participants

3

Reactant 2

HCID 221251942-Chloro-8-fluoroquinolineHCID 867054032-fluoro-N-methyl-4-(3-(piperidin-4-yl)pyrazin-2-yl)benzamide trihydrochloride

Product 1

HCID 72714757HCID 72714757, compound

Procedure

The title compound was prepared analogously to Example 8 by using 2-chloro-8-fluoroquinoline (Combi-blocks) and 2-fluoro-N-methyl-4-(3-(piperidin-4-yl)pyrazin-2-yl)benzamide trihydrochloride (prepared according to Step 2 of Example 1) in Step 3. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.85 (d, J=11.93 Hz, 2H) 2.04-2.19 (m, 2H) 2.91-3.03 (m, 2H) 3.09 (d, J=4.50 Hz, 3H) 3.22 (tt, J=11.61, 3.74 Hz, 1H) 4.72 (d, J=13.50 Hz, 2H) 6.80 (d, J=7.43 Hz, 1H) 7.05 (d, J=9.19 Hz, 1H) 7.08-7.15 (m, 1H) 7.20-7.25 (m, 1H) 7.32-7.39 (m, 2H) 7.44 (dd, J=8.02, 1.37 Hz, 1H) 7.88 (dd, J=9.19, 1.17 Hz, 1H) 8.27 (t, J=8.02 Hz, 1H) 8.50 (d, J=2.35 Hz, 1H) 8.55 (d, J=2.35 Hz, 1H). m/z=460 (M+1).

Sources & evidence

ORD record
ord-f108318b3cfb41089dae88ee868168c9
Source dataset
uspto-grants-2014_04
Patent number
US08691986B2

Reaction notes

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