4-Methoxyphenol → HCID 57919225, compound

HRID 2381311Notes

Reaction equation

HRID 2381311 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:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=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:21]3[CH:22]=[CH:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=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 90154-MethoxyphenolHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919225HCID 57919225, 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 4-methoxy-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(4-methoxy-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid as a light yellow solid (110.8 mg, 87% for the final step). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.06 (br s, 2H), 1.34-1.80 (m, 7H), 1.82-2.08 (m, 1H), 2.10-2.24 (m, 1H), 3.79 (s, 3H), 5.30 (dd, J=10.9, 4.2 Hz, 1H), 5.69 (d, J=2.4 Hz, 1H), 7.05 (d, J=9.1 Hz, 2H), 7.23 (d, J=9.1 Hz, 2H), 8.07 (d, J=2.4 Hz, 1H), 12.98 (br s, 1H).

Sources & evidence

ORD record
ord-4b77d429c7f2491ba04cd22e8e15cd3c
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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