2,6-Dimethylcyclohexanol → HCID 57919266, compound

HRID 2381370Notes

Reaction equation

HRID 2381370 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1Cl.[CH3:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH:19]([CH3:23])[CH:18]1[OH:24].C[O:26][C:27](=[O:36])[CH:28](Br)[CH2:29][CH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1>>[CH:30]1([CH2:29][CH:28]([N:4]2[C:3](=[O:15])[CH:2]=[C:7]([O:24][CH:18]3[CH:19]([CH3:23])[CH2:20][CH2:21][CH2:22][CH:17]3[CH3:16])[CH:6]=[N:5]2)[C:27]([OH:26])=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

4

Reactant 3

HCID 214282,6-DimethylcyclohexanolHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919266HCID 57919266, compound

Procedure

In an analogous manner to the stepwise sequence outlined in Intermediate 72, starting from 4,5-dichloro-2-(tetrahydropyran-2-yl)-2H-pyridazin-3-one (Intermediate 20) and 2,6-dimethyl-cyclohexanol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(2,6-dimethyl-cyclohexyloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (10.5 g, 86% for the final step); LC-MS: 363 (M+1)+, tR=5.03 min. Purity on HPLC: tR=10.3 min, 99.3% (214 nm), 99.0% (254 nm). 1H NMR (300 MHz, DMSO-d6): δ 12.89 (s, 1H), 7.79-7.77 (m, 1H), 6.96-6.82 (m, 1H), 5.36 (dd, 1H, J=10.8 Hz, J=3.9 Hz), 4.58-4.15 (m, 1H), 2.20-0.76 (m, 25H).

Sources & evidence

ORD record
ord-c8d25d21016942d29a4cd1d747cd5959
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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