N-(2-Hydroxybenzoyl)pyrrolidine → HCID 57919304, compound

HRID 2381312Notes

Reaction equation

HRID 2381312 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1Cl.[N:16]1([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[OH:29])=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17]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:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[C:21]([N:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)=[O:22])[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 225361N-(2-Hydroxybenzoyl)pyrrolidineHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919304HCID 57919304, 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-(pyrrolidine-1-carbonyl)-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-{6-oxo-4-[2-(pyrrolidine-1-carbonyl)-phenoxy]-6H-pyridazin-1-yl}-propionic acid as a white solid (100 mg, 32% for the final step). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.91-1.18 (m, 2H), 1.31-1.86 (m, 11H), 1.86-2.05 (m, 1H), 2.06-2.21 (m, 1H), 3.10-3.48 (m, 4H), 5.26 (dd, J=10.7, 4.1 Hz, 1H), 5.77 (d, J=2.4 Hz, 1H), 7.36 (d, J=7.8 Hz, 1H), 7.41 (d, J=7.2 Hz, 1H), 7.47-7.60 (m, 2H), 8.00 (d, J=2.4 Hz, 1H), 13.06 (br s, 1H).

Sources & evidence

ORD record
ord-98bcaaec0dfc4eeba9270adc0a5eea24
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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