5,6,7,8-Tetrahydro-1-naphthol → HCID 57919149, compound

HRID 2381324Notes

Reaction equation

HRID 2381324 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1Cl.[C:16]1([OH:26])[C:25]2[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=2[CH:19]=[CH:18][CH:17]=1.C[O:28][C:29](=[O:38])[CH:30](Br)[CH2:31][CH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1>>[CH:32]1([CH2:31][CH:30]([N:4]2[C:3](=[O:15])[CH:2]=[C:7]([O:26][C:16]3[C:25]4[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=4[CH:19]=[CH:18][CH:17]=3)[CH:6]=[N:5]2)[C:29]([OH:28])=[O:38])[CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

4

Reactant 3

HCID 682585,6,7,8-Tetrahydro-1-naphtholHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919149HCID 57919149, compoundYield 90%

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 5,6,7,8-tetrahydro-naphthalen-1-ol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[6-oxo-4-(5,6,7,8-tetrahydro-naphthalen-1-yloxy)-6H-pyridazin-1-yl]-propionic acid (13.02 g, 90%) as a white solid; LC-MS 383 [M+H+]; HPLC [acetonitrile (0.1% trifluoroacetic acid) in water (0.1% trifluoroacetic acid)=50%˜100%, gradient, 1 mL/min, Venusil MP-C18, C18-15 cm×4.6 mm-5 μm), 254 nm, 95%, 214 nm, 95%. 1H-NMR (300 MHz, CDCl3): δ 7.88 (s, 1H), 7.15 (t, J=7.8 Hz, 1H), 7.03 (d, J=7.8 Hz, 1H), 6.83 (d, J=7.8 Hz, 1H), 5.88 (s, 1H), 5.50 (q, J=4.8 Hz, 1H), 2.81 (s, 2H), 2.55 (s, 2H), 2.17-2.40 (m, 1H), 2.09-2.16 (m, 1H), 1.50-1.90 (m, 11H), 1.14-1.21 (m, 2H).

Sources & evidence

ORD record
ord-7b2417ed826d425ea2d62b5849d71794
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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