2,3-Dihydro-2,2-dimethyl-7-benzofuranol → HCID 57919290, compound

HRID 2381368Notes

Reaction equation

HRID 2381368 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1Cl.[CH3:16][C:17]1([CH3:27])[CH2:21][C:20]2[CH:22]=[CH:23][CH:24]=[C:25]([OH:26])[C:19]=2[O:18]1.C[O:29][C:30](=[O:39])[CH:31](Br)[CH2:32][CH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1>>[CH:33]1([CH2:32][CH:31]([N:4]2[C:3](=[O:15])[CH:2]=[C:7]([O:26][C:25]3[C:19]4[O:18][C:17]([CH3:27])([CH3:16])[CH2:21][C:20]=4[CH:22]=[CH:23][CH:24]=3)[CH:6]=[N:5]2)[C:30]([OH:29])=[O:39])[CH2:37][CH2:36][CH2:35][CH2:34]1

Participants

4

Reactant 3

HCID 152782,3-Dihydro-2,2-dimethyl-7-benzofuranolHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919290HCID 57919290, compound

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 2,2-dimethyl-2,3-dihydro-benzofuran-7-ol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(2,2-dimethyl-2,3-dihydro-benzofuran-7-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid as a white solid (14 g, 91% for the final step); LC-MS: tR=3.73 min, 399 [M+H]+. HPLC: tR=6.52 min, 98.99% at 214 nm, 99.32% at 254 nm. 1H NMR (300 MHz, CD3OD): δ 7.99 (s, 1H), 7.17-6.89 (m, 3H), 5.87 (s, 1H), 5.52-5.48 (m, 1H), 3.12 (s, 2H), 2.40-2.32 (m, 1H), 2.13-2.10 (m, 1H), 1.81-1.52 (m, 7H), 1.45 (s, 6H), 1.20-1.14 (m, 2H).

Sources & evidence

ORD record
ord-cffbf979aed3483399c00e3c06e51917
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

Loading…