3-Phenoxyphenol → HCID 57919146, compound

HRID 2381338Notes

Reaction equation

HRID 2381338 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1Cl.[O:16]([C:23]1[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C[O:31][C:32](=[O:41])[CH:33](Br)[CH2:34][CH:35]1[CH2:39][CH2:38][CH2:37][CH2:36]1>>[CH:35]1([CH2:34][CH:33]([N:4]2[C:3](=[O:15])[CH:2]=[C:7]([O:29][C:25]3[CH:26]=[CH:27][CH:28]=[C:23]([O:16][C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:24]=3)[CH:6]=[N:5]2)[C:32]([OH:31])=[O:41])[CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

4

Reactant 3

HCID 128423-PhenoxyphenolHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919146HCID 57919146, compoundYield 66%

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 3-phenoxy-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[6-oxo-4-(3-phenoxy-phenoxy)-6H-pyridazin-1-yl]-propionic acid (9.0 g, 66%); LC-MS [M+H+]=421; purity>97%, HPLC conditions: C18 column 4.6×112 mm, 5 μm, 1.0 mL/min, acetonitrile (0.1% trifluoroacetic acid) in water (0.1% trifluoroacetic acid)=100%˜50%, detector 214 nm and 254 nm. 1H-NMR (300 MHz, CDCl3): δ 1.09-1.25 (m, 2H), 1.49-1.80 (m, 7H), 2.05-2.17 (m, 1H), 2.29-2.39 (m, 1H), 5.52 (dd, J=4.5, 10.5 Hz, 1H), 6.05 (d, J=2.7 Hz, 1H), 6.73 (s, 1H), 6.82 (d, J=8.1 Hz, 1H), 6.94 (d, J=8.1 Hz, 1H), 7.05-7.20 (m, 3H), 7.27-7.42 (m, 3H), 7.81 (d, J=2.7 Hz, 1H).

Sources & evidence

ORD record
ord-e5b762cfc4e14cdd9118354e0c652157
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

Loading…