2-Chlorophenol → HCID 66875235, compound

HRID 2381408Notes

Reaction equation

I[C:2]1[CH:7]=[N:6][N:5](C2CCCCO2)[C:4](=[O:14])[CH:3]=1.[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[OH:22]>>[Cl:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][C:2]1[CH:7]=[N:6][NH:5][C:4](=[O:14])[CH:3]=1

Participants

Reactant 2

HCID 72452-Chlorophenol

HCID 579192495-Iodo-2-(tetrahydro-2H-pyran-2-yl)pyridazin-3(2H)-one3×

Product 1

HCID 66875235HCID 66875235, compound

Procedure

In an analogous manner to the stepwise sequence outlined in Intermediate 18, starting from 5-iodo-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one (Intermediate 18, step 2) and 2-chloro-phenol afforded 5-(2-chloro-phenoxy)-2H-pyridazin-3-one which was then reacted in an analogous manner to that outlined in the synthesis of Intermediate 19 (steps 4 and 5) alkylating with 2-bromo-3-(tetrahydro-pyran-4-yl)-propionic acid methyl ester (Intermediate 14) to afforded 2-[4-(2-chloro-phenoxy)-6-oxo-6H-pyridazin-1-yl]-3-(tetrahydro-pyran-4-yl)-propionic acid. This material was used crude without further purification in Example 135. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.08-1.38 (m, 3H), 1.45 (d, J=12.4 Hz, 1H), 1.60 (d, J=12.1 Hz, 1H), 1.88-2.00 (m, 1H), 2.04-2.17 (m, 1H), 3.09-3.25 (m, 2H), 3.74-3.85 (m, 2H), 5.42 (dd, J=10.8, 4.4 Hz, 1H), 5.73 (d, J=2.9 Hz, 1H), 7.36-7.47 (m, 1H), 7.47-7.55 (m, 2H), 7.71 (d, J=7.7 Hz, 1H), 8.21 (d, J=2.9 Hz, 1H), 13.10 (br. s., 1H).

Sources & evidence

ORD record: ord-81332687bf494b32b5ef17075b38a157
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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