O-Cresol → HCID 57919284, compound
Reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1Cl.[CH3:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[OH:23].C[O:25][C:26](=[O:35])[CH:27](Br)[CH2:28][CH:29]1[CH2:33][CH2:32][CH2:31][CH2:30]1>>[CH:29]1([CH2:28][CH:27]([N:4]2[C:3](=[O:15])[CH:2]=[C:7]([O:23][C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH3:16])[CH:6]=[N:5]2)[C:26]([OH:25])=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30]1Participants
Procedure
In an analogous manner to the stepwise sequence outlined in intermediate 19, starting from 4,5-dichloro-2-(tetrahydropyran-2-yl)-2H-pyridazin-3-one (Intermediate 20) and 2-methyl-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-(6-oxo-4-o-tolyloxy-6H-pyridazin-1-yl)-propionic acid (12.2 g, 71%) as a white solid; LC-MS [M+H+]=343.2; HPLC (0.17% trifluoroacetic acid in acetonitrile/water, 50%-100% acetonitrile, gradient, 1 mL/min, Venusil MP-C18, C18-15 cm×4.6 mm-5 μm), 254 nm, 98.5%, 214 nm, 99.6%. 1H-NMR (300 MHz, CDCl3) δ 1.12-1.22 (m, 2H), 1.50-1.80 (m, 7H), 2.08-2.16 (m, 1H), 2.20 (s, 3H), 2.30-2.38 (m, 1H), 5.49-5.54 (dd, J=10.2, 4.8 Hz, 1H), 5.85-5.86 (d, J=2.7 Hz, 1H), 7.02-7.04 (d, J=7.2 Hz, 1H), 7.20-7.32 (m, 3H), 7.89-7.90 (d, J=2.7 Hz, 1H).
Sources & evidence
- ORD record
- ord-3e6d10f3b2ac4d9aa456734dfb820dee
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08258134B2
Reaction notes
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