Methyl 2-bromo-3-cyclopentylpropanoate → HCID 57919179, compound

HRID 2381372Notes

Reaction equation

HRID 2381372 reaction equation
[Cl:1][C:2]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:3]=1[O:4][C:5]1[CH:10]=[N:9][NH:8][C:7](=[O:11])[CH:6]=1.C[O:18][C:19](=[O:28])[CH:20](Br)[CH2:21][CH:22]1[CH2:26][CH2:25][CH2:24][CH2:23]1>>[CH:22]1([CH2:21][CH:20]([N:8]2[C:7](=[O:11])[CH:6]=[C:5]([O:4][C:3]3[CH:12]=[CH:13][CH:14]=[C:15]([Cl:16])[C:2]=3[Cl:1])[CH:10]=[N:9]2)[C:19]([OH:28])=[O:18])[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×HCID 66875415HCID 66875415, compound

Product 1

HCID 57919179HCID 57919179, compound

Procedure

In an analogous manner to the stepwise sequence outlined in Intermediate 19 steps 4-5, starting from 5-(2,3-dichloro-phenoxy)-2H-pyridazin-3-one alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(2,3-dichloro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid (12 g, 78% for the final step); LC-MS: 307 [M+1]+, tR=2.50 min. HPLC: 30.31% at 214 nm, 90.71% at 254 nm, tR=3.81 min. 1H NMR (300 MHz, DMSO-d6): δ 8.18 (s, 1H), 7.63 (d, 1H, J=2.1 Hz), 5.79 (d, 1H, J=10.2 Hz), 3.95 (d, 1H, J=12.3 Hz), 3.58 (d, 1H, J=3.3 Hz), 2.04˜1.91 (m, 2H), 1.64˜1.49 (m, 4H).

Sources & evidence

ORD record
ord-1e9c97dab52e41ff8f9d2b763a462bcc
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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