Hydrochloride methanol → HCID 118184911, compound

HRID 2177410Notes

Reaction equation

HRID 2177410 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[C:20]([F:21])=[CH:19][C:18]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[CH:17][C:16]=3[F:27])=[C:11]([C:28]([F:31])([F:30])[F:29])[S:10][N:9]=2)=[C:4]([F:32])[CH:3]=1.Cl.[CH3:34]O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13][O:14][C:15]3[C:20]([F:21])=[CH:19][C:18]([CH2:22][CH2:23][C:24]([O:26][CH3:34])=[O:25])=[CH:17][C:16]=3[F:27])=[C:11]([C:28]([F:31])([F:29])[F:30])[S:10][N:9]=2)=[C:4]([F:32])[CH:3]=1

Participants

3

Reactant 2

HCID 21893726Hydrochloride methanolHCID 90418278GPR120 agonist 4x

Product 1

HCID 118184911HCID 118184911, compound

Procedure

3-(4-((3-(4-Chloro-2-fluorophenyl)-5-(trifluoromethyl)isothiazol-4-yl)methoxy)-3,5-difluorophenyl)propanoic acid (Cpd 74, Example 7; 2 g, 4.04 mmol) in 1 M HCl/MeOH solution (10 mL) was stirred at room temperature for 6 h. The solvent was removed and the residue was partitioned between ethyl acetate and water. The organic layer was washed sequentially with saturated sodium bicarbonate and brine, dried, and filtered. The crude material was purified on a silica gel column, eluting with 10% ethyl acetate/heptanes to afford the desired product as a clear oil. During storage at room temperature, the compound solidified to a white solid (1.86 g, 90%). 1H NMR (400 MHz, CDCl3) δ: 7.55 (d, J=7.5 Hz, 1H), 7.25 (m, J=7.8 Hz, 2H), 6.72 (d, J=6.5 Hz, 2H), 5.10 (s, 2H), 3.70 (s, 3H), 2.82 (t, J=7.2 Hz, 2H), 2.61 (t, J=7.2 Hz, 2H).

Workup

  1. customThe solvent was removed
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed sequentially with saturated sodium bicarbonate and brine
  4. customdried
  5. filtrationfiltered
  6. customThe crude material was purified on a silica gel column
  7. washeluting with 10% ethyl acetate/heptanes

Sources & evidence

ORD record
ord-6a817d48841446e096bcb74b108792b5
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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