HCID 90417900, compound → 3-(4-[[3-(4-Ethylphenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]-3,5-bis(trifluoromethyl)phenyl)propanoic acid

HRID 2177161Notes

Reaction equation

HRID 2177161 reaction equation
CS([O:5][CH2:6][C:7]1[C:8]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH3:23])=[CH:18][CH:17]=2)=[N:9][S:10][C:11]=1[C:12]([F:15])([F:14])[F:13])(=O)=O.O[C:25]1[C:30]([C:31]([F:34])([F:33])[F:32])=[CH:29][C:28]([CH2:35][CH2:36][C:37]([O:39]CC)=[O:38])=[CH:27][C:26]=1[C:42]([F:45])([F:44])[F:43]>>[CH2:22]([C:19]1[CH:20]=[CH:21][C:16]([C:8]2[C:7]([CH2:6][O:5][C:25]3[C:26]([C:42]([F:44])([F:45])[F:43])=[CH:27][C:28]([CH2:35][CH2:36][C:37]([OH:39])=[O:38])=[CH:29][C:30]=3[C:31]([F:32])([F:33])[F:34])=[C:11]([C:12]([F:15])([F:14])[F:13])[S:10][N:9]=2)=[CH:17][CH:18]=1)[CH3:23]

Participants

3

Reactant 2

HCID 90417900HCID 90417900, compoundHCID 90418592HCID 90418592, compound

Product 1

HCID 904185223-(4-[[3-(4-Ethylphenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methoxy]-3,5-bis(trifluoromethyl)phenyl)propanoic acid

Procedure

The title compound was prepared according to the procedure described in Example 1 starting following Step 5 and 6 coupling (3-(4-ethylphenyl)-5-(trifluoromethyl)isothiazol-4-yl)methyl methanesulfonate and ethyl 3-(4-hydroxy-3,5-bis(trifluoromethyl)phenyl)propanoate followed by hydrolysis to afford the desired product as an off-white solid. 1H-NMR (300 Hz, CD3OD): δ 7.75 (s, 1H), 7.69 (s, 1H), 7.46 (d, J=8.4 Hz, 2H), 7.28 (d, J=8.1 Hz, 2H), 5.36 (s, 2H), 2.67-2.74 (m, 4H), 2.45 (t, J=7.2 Hz, 2H), 1.27 (t, J=7.5 Hz, 3H). Mass spectrum (ESI, m/z): Calcd. for C24H18F9NO3S, 572.1 (M+H). found 572.1.

Workup

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

Sources & evidence

ORD record
ord-e4b471c31e4d4514a96f350554c949cb
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

Loading…