2-(Trifluoromethoxy)phenol → HCID 57919165, compound

HRID 2381382Notes

Reaction equation

HRID 2381382 reaction equation
Cl[C:2]1[C:3](=[O:15])[N:4](C2CCCCO2)[N:5]=[CH:6][C:7]=1Cl.[F:16][C:17]([F:27])([F:26])[O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[OH:25].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:25][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[O:18][C:17]([F:26])([F:27])[F:16])[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 27772992-(Trifluoromethoxy)phenolHCID 107292624,5-Dichloro-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one2×HCID 57919172Methyl 2-bromo-3-cyclopentylpropanoate2×

Product 1

HCID 57919165HCID 57919165, 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-trifluoromethoxy-phenol and alkylating with 2-bromo-3-cyclopentyl-propionic acid methyl ester (Intermediate 10) afforded 3-cyclopentyl-2-[6-oxo-4-(2-trifluoromethoxy-phenoxy)-6H-pyridazin-1-yl]-propionic acid as a white solid (14.11 g, 83% for the final step); LC-MS: 413.0 [M+1]+, tR=5.39 min. Purity on HPLC: 97.5% (214 nm), 97.9% (254 nm), tR=8.94 min. 1H NMR (300 MHz, CDCl3): δ 9.90 (s, 1H, broad), 7.89 (d, 1H, J=2.7 Hz), 7.40˜7.33 (m, 3H), 7.24 (s, 1H), 5.96 (d, 1H, J=2.4 Hz), 5.53 (dd, 1H, J1=10.2 Hz J2=4.5 Hz), 2.86˜2.38 (m, 1H), 2.29˜2.07 (m, 1H), 1.79˜1.49 (m, 7H), 1.20˜1.08 (m, 2H).

Sources & evidence

ORD record
ord-aef55fd55d4c4dbfa77a9b33a97e73d2
Source dataset
uspto-grants-2012_09
Patent number
US08258134B2

Reaction notes

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