4-Pyridin-3-yl-benzoic acid → 3-(3-Cyanophenyl)-2-[1-(4-pyridin-3-ylbenzoyl)-pyrrolidin-2-yl]propionic acid methyl ester
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)[CH:2]=1.[CH3:16][O:17][C:18](=[O:34])[CH:19]([CH:29]1[CH2:33][CH2:32][CH2:31][NH:30]1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]#[N:28])[CH:22]=1>>[CH3:16][O:17][C:18](=[O:34])[CH:19]([CH:29]1[CH2:33][CH2:32][CH2:31][N:30]1[C:11](=[O:13])[C:10]1[CH:9]=[CH:8][C:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:15][CH:14]=1)[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]#[N:28])[CH:22]=1Participants
3
Procedure
4-Pyridin-3-ylbenzoic acid (0.83 g, 3.5 mmol) and 3-(3-cyanophenyl)-2-(pyrrolidin-2-yl)-propionic acid methyl ester (0.91 g, 3.5 mmol) are coupled as described in EXAMPLE 1B to give the title compound (1.22 g, 2.8 mmol). 1H NMR (CDCl3, 300 MHz) □ 8.98(s, 1H), 8.75(d, 1H), 8.58(d, 1H), 8.03(m, 1H), 7.85-7.60(m, 4H), 4.72-4.45(two m, 1H), 3.80-3.71(m, 1H), 3.68, 3.62(two s, 3H), 3.63-3.40(m, 2H), 3.21-3.10(m, 1H), 2.90-2.78(m, 1H), 2.20-2.05(m, 1H), 2.02-1.50(m, 3H).
Sources & evidence
- ORD record
- ord-0434dc07662648e1a0989e12149bde16
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07361663B2
Reaction notes
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