Cyclopentanol → HCID 57919227, compound

HRID 2381358Notes

Reaction equation

HRID 2381358 reaction equation
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:8]1[C:9](=[O:21])[N:10](C2CCCCO2)[N:11]=[CH:12][C:13]=1Cl.C[O:23][C:24](=[O:33])[CH:25](Br)[CH2:26][CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1>>[CH:27]1([CH2:26][CH:25]([N:10]2[C:9](=[O:21])[CH:8]=[C:13]([O:6][CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:12]=[N:11]2)[C:24]([OH:23])=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

4

Reactant 3

HCID 7298CyclopentanolHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919227HCID 57919227, compound

Procedure

In an analogous manner to the stepwise sequence outlined in Intermediate 59, starting from cyclopentanol and 4,5-dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one (Intermediate 20) and 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-(4-cyclopentyloxy-6-oxo-6H-pyridazin-1-yl)-propionic acid as a white solid (244.7 mg, 88%, total or for last step); ES+-HRMS m/e calcd for C17H24N2O4 [M+H+] 321.1809, found 321.1808. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.96-1.17 (m, 2H), 1.35-1.78 (m, 13H), 1.87-2.01 (m, 3H), 2.15 (ddd, J=13.8, 11.0, 5.0 Hz, 1H), 4.81-4.90 (m, 1H), 5.31 (dd, J=11.0, 4.2 Hz, 1H), 6.26 (d, J=2.8 Hz, 1H), 7.75 (d, J=2.8 Hz, 1H), 12.92 (br s, 1H).

Sources & evidence

ORD record
ord-9a59fcd4021e473694e920271da05621
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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