HCID 59419852, compound → 3-(4-[[3-(4-Chlorophenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]-3,5-difluorophenyl)-2-methylpropanoic acid

HRID 2177175Notes

Reaction equation

HRID 2177175 reaction equation
CS([O:5][CH2:6][C:7]1[C:8]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[N:9][S:10][C:11]=1[C:12]([F:15])([F:14])[F:13])(=O)=O.[F:23][C:24]1[CH:25]=[C:26]([CH2:32][CH:33]([CH3:39])[C:34]([O:36]CC)=[O:35])[CH:27]=[C:28]([F:31])[C:29]=1O>>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:8]2[C:7]([CH2:6][O:5][C:29]3[C:28]([F:31])=[CH:27][C:26]([CH2:32][CH:33]([CH3:39])[C:34]([OH:36])=[O:35])=[CH:25][C:24]=3[F:23])=[C:11]([C:12]([F:15])([F:14])[F:13])[S:10][N:9]=2)=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 59419852HCID 59419852, compoundHCID 90418265HCID 90418265, compound

Product 1

HCID 854724893-(4-[[3-(4-Chlorophenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]-3,5-difluorophenyl)-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-(4-chlorophenyl)-5-(trifluoromethyl)isothiazol-4-yl)methyl methanesulfonate and ethyl 3-(3,5-difluoro-4-hydroxyphenyl)-2-methylpropanoate (prepared according to PCT Application WO2010/048207A2) followed by hydrolysis to afford the desired product as an off-white solid. 1H NMR (300 MHz, CD3OD): δ 7.76 (d, J=8.4 Hz, 2H), 7.52 (d, J=8.4 Hz, 2H), 6.81 (d, J=9.6 Hz, 2H), 5.18 (s, 2H), 2.88-2.93 (m, 1H), 2.51-2.59 (m, 2H), 1.11 (d, J=6.3 Hz, 3H). Mass spectrum (ESI, m/z): Calcd. for: C21H15ClF5NO3S: 492.0 (M+H). found 492.0.

Workup

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

Sources & evidence

ORD record
ord-cdb1a7e103434831bdf3a817dde88eb1
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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