Methyl 2-bromo-3-cyclopentylpropanoate → HCID 57919213, compound

HRID 2381375Notes

Reaction equation

HRID 2381375 reaction equation
Cl[C:2]1[C:3](=[O:19])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1[O:8][CH:9]1[CH2:12][CH2:11][CH2:10]1.C[O:21][C:22](=[O:31])[CH:23](Br)[CH2:24][CH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>>[CH:9]1([O:8][C:7]2[CH:6]=[N:5][N:4]([CH:23]([CH2:24][CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[C:22]([OH:21])=[O:31])[C:3](=[O:19])[CH:2]=2)[CH2:12][CH2:11][CH2:10]1

Participants

3

Reactant 2

HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×HCID 66875264HCID 66875264, compound

Product 1

HCID 57919213HCID 57919213, compound

Procedure

In an analogous manner to the stepwise sequence outlined in intermediate 19 (steps 2-5), starting from 4-chloro-5-cyclobutoxy-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 2-(4-cyclobutoxy-6-oxo-6H-pyridazin-1-yl)-3-cyclopentyl-propionic acid (9.0 g, 98% for the final step); LC-MS: 307 (M+1)+, tR=4.17 min. HPLC: tR=12.71 min, (214 nm, 98.6%), (254 nm, 99.0%). 1H NMR (300 MHz, DMSO-d6): δ 12.86 (s, 1H, broad), 7.80 (d, 1H J=4.8 Hz), 6.61 (d, 1H, J=5.1 Hz), 5.36 (dd, 1H, J=10.8 Hz, J=3.9 Hz), 4.58-4.14 (m, 1H), 2.20-0.76 (m, 17H).

Sources & evidence

ORD record
ord-a66c901fda074fff801a04e65104cec4
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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