1,4-Dioxane hydrochloride → HCID 86680480, compound

HRID 2406441Notes

Reaction equation

HRID 2406441 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.[ClH:22].O1CCOCC1>C(O)C>[ClH:22].[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 204431481,4-Dioxane hydrochlorideHCID 715443511429329-63-4

Product 1

HCID 86680480HCID 86680480, compoundYield 72%

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 (120 ml) was added 1,4-dioxane HCl (4 M, 1.66 mL, 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 hydrochloride as an off-white solid (1.6 g, 71% yield), HPLC purity 99.7%, mp 229-232° C. 1H NMR (400 MHz, DMSO-d6): 8.81 (d, 2H), 8.04 (d, 2H), 7.92-7.89 (m, 3H), 7.29 (t, 2H), 7.13 (br s, 1H), 2.00 (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-080236f578c1467b80ba66f6b9389577
Source dataset
uspto-grants-2014_08
Patent number
US08809372B2

Reaction notes

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