Ethyl 2-(3,5-difluoro-4-hydroxyphenyl)cyclopropanecarboxylate → HCID 90418329, compound

HRID 2177243Notes

Reaction equation

HRID 2177243 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.[F:24][C:25]1[CH:26]=[C:27]([CH:33]2[CH2:35][CH:34]2[C:36]([O:38]CC)=[O:37])[CH:28]=[C:29]([F:32])[C:30]=1O>>[CH2:22]([C:19]1[CH:20]=[CH:21][C:16]([C:8]2[C:7]([CH2:6][O:5][C:30]3[C:29]([F:32])=[CH:28][C:27]([CH:33]4[CH2:35][CH:34]4[C:36]([OH:38])=[O:37])=[CH:26][C:25]=3[F:24])=[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 59419842Ethyl 2-(3,5-difluoro-4-hydroxyphenyl)cyclopropanecarboxylateHCID 90418592HCID 90418592, compound

Product 1

HCID 90418329HCID 90418329, compound

Procedure

The title compound was prepared according to the procedure described in Example 1 following Steps 5 and 6 by coupling [3-(4-ethylphenyl)-5-(trifluoromethyl)-1,2-thiazol-4-yl]methyl methanesulfonate and ethyl 2-(3,5-difluoro-4-hydroxyphenyl)cyclopropane-1-carboxylate followed by hydrolysis to afford the desired product as an off-white solid. 1HNMR (300 MHz, CDCl3) δ 7.75 (d, J=8.1 Hz, 2H), 7.32 (d, J=8.1 Hz, 2H), 6.63-6.71 (m, 2H), 5.16 (s, 2H), 2.69-2.77 (m, 2H), 2.49-2.55 (m, 2H), 1.64-1.89 (m, 2H), 1.29-1.37 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C23H18F5NO3S, 482.1[M−H]. found 482.1.

Workup

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

Sources & evidence

ORD record
ord-fbc07d260d224a949ad3f217f4c2e5fc
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

Loading…