2-morpholinophenol → HCID 57919123, compound

HRID 2381342Notes

Reaction equation

HRID 2381342 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1Cl.[N:16]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[OH:28])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C[O:30][C:31](=[O:40])[CH:32](Br)[CH2:33][CH:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1>>[CH:34]1([CH2:33][CH:32]([N:4]2[C:3](=[O:15])[CH:2]=[C:7]([O:28][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[N:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[CH:6]=[N:5]2)[C:31]([OH:30])=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

4

Reactant 3

HCID 27953942-morpholinophenolHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919123HCID 57919123, compoundYield 64%

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 2-morpholin-4-yl-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(2-morpholin-4-yl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (8.5 g, 64%) as a white solid; LC-MS: 414 [M+H+]. HPLC: >99% (purity). 1H-NMR (300 MHz, DMSO-d6): δ 12.9 (s, 1H), 8.00 (s, 1H), 7.1-7.3 (m, 4H), 5.76 (s, 1H), 5.3 (m, 1H); 3.3 (m, 4H), 2.9 (m, 4H), 1.0-2.2 (m, 11H).

Sources & evidence

ORD record
ord-899fe3cf92a94e139c2bd52f4326afce
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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