N-(4-fluorobenzyl)ethanamine → HCID 90407392, compound
Reaction equation
CS(O[CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[C:17]([C:19]([O:21]C)=[O:20])[CH:16]=[CH:15][N:14]=2)[N:10]=[CH:9]1)(=O)=O.[F:23][C:24]1[CH:33]=[CH:32][C:27]([CH2:28][NH:29][CH2:30][CH3:31])=[CH:26][CH:25]=1>>[CH2:30]([N:29]([CH2:28][C:27]1[CH:26]=[CH:25][C:24]([F:23])=[CH:33][CH:32]=1)[CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[C:17]([C:19]([OH:21])=[O:20])[CH:16]=[CH:15][N:14]=2)[N:10]=[CH:9]1)[CH3:31]Participants
3
Procedure
The title compound was prepared in 14% yield from methyl 2-(1-{2-[(methylsulfonyl)oxy]ethyl}-1H-imidazol-4-yl)pyridine-4-carboxylate (PREPARATION 6) and 4-fluoro-N-ethylbenzylamine according to the procedure for the preparation of Example 58. 1HNMR (400 MHz, DMSO): δ 0.90 (3H, t, J=6.9 Hz), 2.74 (2H, t, J=6.4 Hz), 3.58 (2H, s), 4.08 (2H, t, J=5.9 Hz), 7.03 (2H, t, J=8.9 Hz), 7.23 (2H, dd, J=7.0 Hz and 2.6 Hz), 7.43 (1H, d, J=5.2 Hz), 7.66 (1H, d, J=4.4 Hz), 8.21 (1H, s), 8.35 (1H, d, J=4.5 Hz), 8.54 (1H, s). [M+H] Calc'd for C20H21FN4O2, 369. Found, 369.
Sources & evidence
- ORD record
- ord-853a57dadfd64961bc561077cd830ba9
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133166B2
Reaction notes
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