p-Toluenesulfonic acid → HCID 86680481, compound

HRID 2406442Notes

Reaction equation

HRID 2406442 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:13]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)([OH:15])[CH3:14])=[CH:11][N:12]=2)=[CH:4][CH:3]=1.[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([S:29]([OH:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1>C(O)C>[CH3:22][C:23]1[CH:24]=[CH:25][C:26]([S:29]([OH:32])(=[O:31])=[O:30])=[CH:27][CH:28]=1.[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:13]([C:16]3[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=3)([OH:15])[CH3:14])=[CH:11][N:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 715443511429329-63-4

Product 1

HCID 86680481HCID 86680481, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 1-(2-(4-fluorophenyl)-thiazol-5-yl)-1-(pyridin-4-yl)ethanol (2 g, 6.6 mmol) in ethanol (60 mL) was added 4-methylbenzenesulfonic acid (1.14 g, 6.6 mmol) slowly at 0° C., and then the mixture was stirred for 1 hour at room temperature. The solid that formed was filtered and washed with hexane (10 mL) to afford 4-(1-(1-(2-(4-fluorophenyl)thiazol-5-yl)-1-(pyridin-4-yl)ethanol 4-methylbenzenesulfonic acid salt as an off-white solid (1.9 g, 61% yield), HPLC purity 98.2%, mp 181-184° C. 1H NMR (400 MHz, DMSO-d6): 8.84 (d, 2H), 8.08 (d, 2H), 7.91 (t, 3H), 7.46 (d, 2H), 7.30 (t, 2H), 7.09 (d, 2H), 2.26 (s, 3H), 2.01 (s, 3H); LC-MS m/z calculated for [M+H]+ 301.07, found 301.1.

Workup

  1. customThe solid that formed
  2. filtrationwas filtered
  3. washwashed with hexane (10 mL)

Sources & evidence

ORD record
ord-f85d0d365f2a4925a7887afc84355434
Source dataset
uspto-grants-2014_08
Patent number
US08809372B2

Reaction notes

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