Phenol, 2-fluoro-5-methyl- → HCID 57919187, compound

HRID 2381384Notes

Reaction equation

HRID 2381384 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1Cl.[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[OH:24].C[O:26][C:27](=[O:36])[CH:28](Br)[CH2:29][CH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1>>[CH:30]1([CH2:29][CH:28]([N:4]2[C:3](=[O:15])[CH:2]=[C:7]([O:24][C:18]3[CH:19]=[C:20]([CH3:23])[CH:21]=[CH:22][C:17]=3[F:16])[CH:6]=[N:5]2)[C:27]([OH:26])=[O:36])[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

4

Reactant 3

HCID 182387Phenol, 2-fluoro-5-methyl-HCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919187HCID 57919187, 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-fluoro-5-methyl-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[4-(2-fluoro-5-methyl-phenoxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid as a white solid (14.5 g, 74% for the final step); LC-MS: 361 [M+1]+, tR=5.20 min. Purity on HPLC: 98.2% (214 nm), 98.9% (254 nm), tR=8.93 min. 1H NMR (300 MHz, CDCl3): δ9.54 (s, 1H broad), 7.89 (d, 1H, J=2.1), 7.14˜7.08 (m, 2H), 6.99 (d, 1H, J=9.0), 5.98 (s, 1H), 5.53 (dd, 1H J1=10.5 Hz, J2=4.5 Hz), 2.35 (s, 3H), 2.39˜2.20 (m, 1H), 2.15˜2.06 (m, 1H), 1.79˜1.49 (m, 7H), 1.20˜1.11 (m, 3H).

Sources & evidence

ORD record
ord-3b6f096b82de440cbe213a80306ce70d
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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