HCID 59419852, compound → 3-(3,5-Difluoro-4-[[3-(2-fluoro-4-methylphenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]phenyl)-2-methylpropanoic acid

HRID 2177188Notes

Reaction equation

HRID 2177188 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:13]([CH2:14][OH:15])=[C:12]([C:16]([F:19])([F:18])[F:17])[S:11][N:10]=1.[F:20][C:21]1[CH:22]=[C:23]([CH2:29][CH:30]([CH3:36])[C:31]([O:33]CC)=[O:32])[CH:24]=[C:25]([F:28])[C:26]=1O>>[F:20][C:21]1[CH:22]=[C:23]([CH2:29][CH:30]([CH3:36])[C:31]([OH:33])=[O:32])[CH:24]=[C:25]([F:28])[C:26]=1[O:15][CH2:14][C:13]1[C:9]([C:3]2[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[F:1])=[N:10][S:11][C:12]=1[C:16]([F:19])([F:17])[F:18]

Participants

3

Reactant 2

HCID 59419852HCID 59419852, compoundHCID 90418878(3-(2-Fluoro-4-methylphenyl)-5-(trifluoromethyl)isothiazol-4-yl)methanol

Product 1

HCID 784260523-(3,5-Difluoro-4-[[3-(2-fluoro-4-methylphenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]phenyl)-2-methylpropanoic acid

Procedure

The title compound was prepared according to the procedure described in Example 1 starting following Step 5 and 6 coupling (3-(2-fluoro-4-methylphenyl)-5-(trifluoromethyl)isothiazol-4-yl)methanol and ethyl 3-(3,5-difluoro-4-hydroxyphenyl)-2-methylpropanoate followed by hydrolysis to afford the desired product as an off-white solid. 1H NMR (300 MHz, CD3OD) δ 7.29 (t, J=7.8 Hz, 1H), 7.10 (d, J=7.5 Hz, 1H), 7.07 (d, J=11.4 Hz, 1H), 6.73 (d, J=9.7 Hz, 2H), 5.13 (s, 2H), 2.94-2.85 (m, 1H), 2.54-2.44 (m, 2H), 2.44 (s, 3H), 1.09 (d, J=6.3 Hz, 3H). Mass spectrum (ESI, m/z): Calcd. for C22H17F6NO3S, 488.1 (M−H). found 488.1.

Workup

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

Sources & evidence

ORD record
ord-26b44c811c374c20bfd5539beb97b5d3
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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