Isoquinolin-5-ol → HCID 57919137, compound

HRID 2381345Notes

Reaction equation

HRID 2381345 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1Cl.[CH:16]1[C:25]2[CH:24]=[CH:23][CH:22]=[C:21]([OH:26])[C:20]=2[CH:19]=[CH:18][N: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:21]3[CH:22]=[CH:23][CH:24]=[C:25]4[C:20]=3[CH:19]=[CH:18][N:17]=[CH:16]4)[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 30386Isoquinolin-5-olHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919137HCID 57919137, compoundYield 73%

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 isoquinolin-5-ol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(isoquinolin-5-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (10.1 g, 73%) as a brown solid; ESI-MS 380 [M+H+]; HPLC: >96% (purity). 1H-NMR (300 MHz, DMSO-d6): δ 1.11 (m, 2H), 1.52 (m, 7H), 2.01 (m, 1H), 2.22 (m, 1H), 5.32 (m, 1H), 5.89 (s, 1H), 7.77 (m, 3H), 8.14 (m, 1H), 8.27 (m, 1H), 8.59 (m, 1H), 9.46 (s, 1H), 13.00 (s, 1H).

Sources & evidence

ORD record
ord-80c6aae85cb24dbeb31a36e172cbfc34
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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