Ethyl Acetate → HCID 24851979, compound

HRID 599599Notes

Reaction equation

HRID 599599 reaction equation
CCN(S(F)(F)[F:7])CC.[F:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][CH2:20][N:19]3[N:23]=[C:24](/[CH:26]=[CH:27]/[C:28]4[CH:33]=[CH:32][C:31]([N:34]5[CH:38]=[C:37]([CH3:39])[N:36]=[CH:35]5)=[C:30]([O:40][CH3:41])[CH:29]=4)[N:25]=[C:18]23)=[CH:13][CH:12]=1.C(OCC)(=O)C.O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[F:7][C:17]1([C:14]2[CH:13]=[CH:12][C:11]([F:10])=[CH:16][CH:15]=2)[CH2:22][CH2:21][CH2:20][N:19]2[N:23]=[C:24](/[CH:26]=[CH:27]/[C:28]3[CH:33]=[CH:32][C:31]([N:34]4[CH:38]=[C:37]([CH3:39])[N:36]=[CH:35]4)=[C:30]([O:40][CH3:41])[CH:29]=3)[N:25]=[C:18]12.[F:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[C:18]3[N:19]([N:23]=[C:24](/[CH:26]=[CH:27]/[C:28]4[CH:33]=[CH:32][C:31]([N:34]5[CH:38]=[C:37]([CH3:39])[N:36]=[CH:35]5)=[C:30]([O:40][CH3:41])[CH:29]=4)[N:25]=3)[CH2:20][CH2:21][CH:22]=2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 123472(Diethylamino)sulfur trifluorideHCID 24852898HCID 24852898, compoundHCID 86585896Sodium bicarbonate water

Product 2

HCID 24851979HCID 24851979, compoundHCID 24852097HCID 24852097, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

DAST (0.04 mL) was added to a solution of (+)-8-(4-fluorophenyl)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridine synthesized by the method in Example 51 (51 mg) in methylene chloride (2 mL) at 0° C., and the reaction solution was stirred at 0° C. for one hour. Ethyl acetate and saturated sodium bicarbonate water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was separated by CHIRALPAK™ IA manufactured by Daicel Chemical Industries, Ltd. (2 cm×25 cm; mobile phase: hexane:ethanol=1:1) to obtain (+)-8-fluoro-8-(4-fluorophenyl)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridine with a retention time of 11 minutes (6 mg, >99% ee), (−)-8-fluoro-8-(4-fluorophenyl)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-5,6,7,8-tetrahydro[1,2,4]triazolo[1,5-a]pyridine with a retention time of 12 minutes (5 mg, >99% ee) and 8-(4-fluorophenyl)-2-{(E)-2-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]vinyl}-5,6-dihydro[1,2,4]triazolo[1,5-a]pyridine with a retention time of 14 minutes (2 mg).

Workup

  1. customthe organic layer was separated
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was separated by CHIRALPAK™ IA

Sources & evidence

ORD record
ord-394fac26318e4bbeaf4ae1cab8299f5d
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

Loading…