Potassium Carbonate → HCID 69673709, compound

HRID 2283248Notes

Reaction equation

HRID 2283248 reaction equation
[OH:1][CH2:2][CH:3]([NH:5][C:6]([C:8]1[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:12][N:11]=[N:10][C:9]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O)[CH3:4].CCN(S(F)(F)F)CC.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[C:20]1([C:9]2[N:10]=[N:11][CH:12]=[C:13]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:8]=2[CH:6]2[NH:5][C:3]([CH3:4])=[CH:2][O:1]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123472(Diethylamino)sulfur trifluorideHCID 69673872HCID 69673872, compound

Product 1

HCID 69673709HCID 69673709, compoundYield 63.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(1-hydroxy propan-2-yl)-3,5-diphenylpyridazine-4-carboxamide (150 mg, 0.45 mmol) in DCM (8 mL), DAST (145 mg, 0.90 mmol) was added at −78° C. and stirred for 2 h. After completion of starting materials, solid K2CO3 (248 mg, 1.80 mmol) was added to the reaction mixture at −78° C. and stirred at rt for 4 h. The reaction mixture was diluted with DCM (20 mL), washed with water (2×8 mL), saturated NaHCO3 (1×5 mL), water (1×5 mL), brine (1×2 mL) and dried over anhy. Na2SO4. Evaporation of the solvent under reduced pressure gave the crude product which was purified by column chromatography (100-200 mesh silica gel, 35% EtOAc-Hexane) to furnish 2-(3, 5-diphenylpyridazin-4-yl)-4-methyldihydrooxazole (compound 21) (90 mg, 63%) as pale yellow solid.

Workup

  1. stirringstirred at rt for 4 h
  2. washwashed with water (2×8 mL), saturated NaHCO3 (1×5 mL), water (1×5 mL), brine (1×2 mL)
  3. customdried over anhy
  4. customEvaporation of the solvent under reduced pressure
  5. customgave the crude product which
  6. customwas purified by column chromatography (100-200 mesh silica gel, 35% EtOAc-Hexane)

Sources & evidence

ORD record
ord-7157343736ce4c2eba7ef2e5738af6a4
Source dataset
uspto-grants-2015_09
Patent number
US09145372B2

Reaction notes

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