(S)-Methyl 4-(1-aminoethyl)benzoate hydrochloride → Methyl 4-[(1S)-1-({[5-fluoro-2-(4-fluorobenzyl)pyridin-3-yl]carbonyl}amino)ethyl]benzoate
Reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.Cl.[NH2:20][C@H:21]([C:23]1[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=1)[CH3:22]>>[F:1][C:2]1[CH:10]=[C:6]([C:7]([NH:20][C@H:21]([C:23]2[CH:32]=[CH:31][C:26]([C:27]([O:29][CH3:30])=[O:28])=[CH:25][CH:24]=2)[CH3:22])=[O:9])[C:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[N:4][CH:3]=1Participants
3
Procedure
The title compound was prepared according to the procedure described in step 3 of Example 1 from 5-fluoro-2-(4-fluorobenzyl)nicotinic acid (step 3 of Example 58) and methyl 4-[(1S)-1-aminoethyl]benzoate hydrochloride (step 3 of Example 5): 1H-NMR (CDCl3) δ 9.13 (1H, d, J=7.7 Hz), 8.59 (1H, d, J=3.0 Hz), 7.93 (2H, d, J=8.4 Hz), 7.79 (1H, dd, J=8.7, 2.8 Hz), 7.51 (2H, d, J=8.2 Hz), 7.15–7.09 (2H, m), 7.03–6.96 (2H, m), 5.19–5.09 (1H, m), 4.17 (1H, d, J=13.7 Hz), 4.08 (1H, d, J=13.7 Hz), 3.85 (3H, s), 1.42 (3H, d, J=7.1 Hz); MS (ESI) m/z 411 (M+H)+, 409 (M−H)−.
Sources & evidence
- ORD record
- ord-21abcc417d8a445c995877e3f8ab38ef
- Source dataset
- uspto-grants-2007_07
- Patent number
- US07238714B2
Reaction notes
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