3-Methoxyphenol → HCID 57919124, compound

HRID 2381310Notes

Reaction equation

HRID 2381310 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1Cl.[CH3:16][O:17][C:18]1[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=1.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][C:20]3[CH:21]=[CH:22][CH:23]=[C:18]([O:17][CH3:16])[CH:19]=3)[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 90073-MethoxyphenolHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919124HCID 57919124, 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 3-methoxy-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(3-methoxy-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid as a white solid (159.4 mg, 42% for the final step); ES+-HRMS m/e calcd for C19H22N2O5 [M+H+] 359.1602, found 359.1600. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.04 (br s, 2H), 1.31-1.80 (m, 7H), 1.87-2.09 (m, 1H), 2.09-2.25 (m, 1H), 3.78 (s, 3H), 5.31 (dd, J=11.0, 4.1 Hz, 1H), 5.79 (d, J=2.7 Hz, 1H), 6.85 (dd, J=7.8, 1.8 Hz, 1H), 6.89-6.96 (m, 2H), 7.42 (t, J=8.2 Hz, 1H), 8.08 (d, J=2.7 Hz, 1H), 13.03 (br s, 1H).

Sources & evidence

ORD record
ord-8ef919e2b0db4dc9992f908c7ea4ffae
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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