(Diethylamino)sulfur trifluoride → HCID 66839578, compound

HRID 546773Notes

Reaction equation

HRID 546773 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7](/[CH:9]=[CH:10]/[C:11]2[N:27]=[C:14]3[CH:15]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[CH2:25]O)[CH2:16][CH2:17][CH2:18][N:13]3[N:12]=2)[CH:6]=[CH:5][C:4]=1[N:28]1[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]1.CCN(S(F)(F)[F:40])CC.O.C(=O)(O)[O-].[Na+]>ClCCl>[F:40][CH2:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH:15]1[CH2:16][CH2:17][CH2:18][N:13]2[N:12]=[C:11](/[CH:10]=[CH:9]/[C:7]3[CH:6]=[CH:5][C:4]([N:28]4[CH:32]=[C:31]([CH3:33])[N:30]=[CH:29]4)=[C:3]([O:2][CH3:1])[N:8]=3)[N:27]=[C:14]12

Participants

5

Reactant 3

HCID 123472(Diethylamino)sulfur trifluorideHCID 66839482HCID 66839482, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 66839578HCID 66839578, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

{2-{2-{(E)-2-[6-methoxy-5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]vinyl}-5,6,7,8-tetrahydro-[1,2,4]triazolo[1,5-a]pyridin-8-yl}phenyl}methanol (350 mg) was dissolved in dichloromethane (40 mL). This was added dropwise to a solution of DAST (1.04 mL) in dichloromethane (6 mL) cooled to −78° C., and the reaction solution was stirred for one hour. Saturated sodium bicarbonate water was added to the reaction solution, followed by extraction with dichloromethane. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (carrier: NH silica, elution solvent: ethyl acetate:methanol=9:1) to obtain a racemate of the title compound (70 mg). The resulting racemate was separated by CHIRALPAK™ IB manufactured by Daicel Chemical Industries, Ltd. (2 cm×25 cm, mobile phase: ethanol, flow rate: 10 mL/min) to obtain the title optically active compound with a retention time of 7 minutes and positive optical rotation (20 mg) and the title optically active compound with a retention time of 9 minutes and negative optical rotation (20 mg), where the retention time is an analysis result in CHIRALPAK™ IB manufactured by Daicel Chemical Industries, Ltd. (Lot. IB00CD-FD026, mobile phase: ethanol, flow rate: 0.5 mL/min).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel chromatography (carrier: NH silica, elution solvent: ethyl acetate:methanol=9:1)

Sources & evidence

ORD record
ord-4519d66d7a064731a26b669ac571423b
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

Loading…