2,3,6-Trimethylphenol → HCID 57919168, compound

HRID 2381367Notes

Reaction equation

HRID 2381367 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[C:22]([CH3:23])=[CH:21][CH:20]=[C:19]([CH3:24])[C:18]=1[OH:25].C[O:27][C:28](=[O:37])[CH:29](Br)[CH2:30][CH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1>>[CH:31]1([CH2:30][CH:29]([N:4]2[C:3](=[O:15])[CH:2]=[C:7]([O:25][C:18]3[C:19]([CH3:24])=[CH:20][CH:21]=[C:22]([CH3:23])[C:17]=3[CH3:16])[CH:6]=[N:5]2)[C:28]([OH:27])=[O:37])[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

4

Reactant 3

HCID 170162,3,6-TrimethylphenolHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919168HCID 57919168, compound

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 2,3,6-trimethyl-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[6-oxo-4-(2,3,6-trimethyl-phenoxy)-6H-pyridazin-1-yl]-propionic acid as a white solid (11.5 g, 58% for the final step); LC-MS 371 [M+1]+, tR=3.92 min. Purity on HPLC: 98.5% (214 nm), 99.2% (254 nm), tR=9.92 min. 1H NMR (300 MHz, CDCl3): δ 7.94 (d, 1H, J=2.7 Hz), 7.02 (s, 2H), 5.74 (d, 1H, J=2.7 Hz), 5.52 (dd, 1H, J1=10.2 Hz, J2=5.4 Hz), 2.34˜2.32 (m, 1H), 2.20˜2.16 (m, 1H), 2.29 (s, 3H), 2.18 (s, 3H), 2.05 (s, 3H), 1.79˜1.49 (m, 7H), 1.25˜1.14 (m, 2H).

Sources & evidence

ORD record
ord-36a3cda8361040409c97717228c02fa0
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

Loading…