Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate → HCID 90418729, compound

HRID 2177163Notes

Reaction equation

HRID 2177163 reaction equation
CS([O:5][CH2:6][C:7]1[C:8]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([F:24])[CH:17]=2)=[N:9][S:10][C:11]=1[C:12]([F:15])([F:14])[F:13])(=O)=O.O[C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]([O:36]CC)=[O:35])=[C:28]([CH3:39])[C:27]=1[CH3:40]>>[F:24][C:18]1[CH:17]=[C:16]([C:8]2[C:7]([CH2:6][O:5][C:26]3[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]([OH:36])=[O:35])=[C:28]([CH3:39])[C:27]=3[CH3:40])=[C:11]([C:12]([F:15])([F:14])[F:13])[S:10][N:9]=2)[CH:21]=[CH:20][C:19]=1[O:22][CH3:23]

Participants

3

Reactant 2

HCID 58566491Ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoateHCID 90418146HCID 90418146, compound

Product 1

HCID 90418729HCID 90418729, compound

Procedure

The title compound was prepared according to the procedure described in Example 1 starting following Step 5 and 6 coupling (5-(trifluoromethyl)-3-(3-fluoro-4-methoxyphenyl)isothiazol-4-yl)methyl methanesulfonate and ethyl 3-(4-hydroxy-2,3-dimethylphenyl)propanoate followed by hydrolysis to afford the desired product as an off-white solid. 1H NMR (300 MHz, DMSO) δ 12.12 (s, 1H), 7.48-7.58 (m, 2H), 7.31 (t, J=8.7 Hz, 2H), 6.96 (d, J=8.4 Hz, 1H), 6.80 (d, J=8.4 Hz, 1H), 5.09 (s, 2H), 3.89 (s, 3H), 2.76 (t, J=7.2 Hz, 2H), 2.41 (t, J=7.5 Hz, 2H), 2.14 (s, 3H), 1.97 (s, 3H). Mass spectrum (ESI, m/z): Calcd. for C23H21F4NO4S, 482.1 (M−H). found 482.0.

Workup

  1. customThe title compound was prepared
  2. customfollowed by hydrolysis

Sources & evidence

ORD record
ord-2866e19f3c3d44b5bfec4b0bb8e6731f
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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