Triethylamine → HCID 57593116, compound

HRID 1784501Notes

Reaction equation

HRID 1784501 reaction equation
[C:1]1([C:7]23[CH2:14][CH2:13][C:10]([C:15]([OH:17])=O)([CH2:11][CH2:12]2)[CH2:9][CH2:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[CH2:24]([O:31][C:32]1[CH:41]=[CH:40][C:35]([C:36]([NH:38][NH2:39])=[O:37])=[C:34]([C:42]([F:45])([F:44])[F:43])[CH:33]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[CH2:24]([O:31][C:32]1[CH:41]=[CH:40][C:35]([C:36]([NH:38][NH:39][C:15]([C:10]23[CH2:9][CH2:8][C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)([CH2:14][CH2:13]2)[CH2:12][CH2:11]3)=[O:17])=[O:37])=[C:34]([C:42]([F:43])([F:44])[F:45])[CH:33]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 126177784-Phenylbicyclo[2.2.2]octane-1-carboxylic acidHCID 22591719HCID 22591719, compound

Product 1

HCID 57593116HCID 57593116, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a magnetically stirred solution of 4-phenylbicyclo[2.2.2]octane-1-carboxylic acid (8-A) (70 mg, 0.30 mmol) in methylene chloride (1 mL) at room temperature was added 2 M oxalyl chloride in methylene chloride (0.61 mL, 1.22 mmol). Two drops of catalytic DMF were added to catalyze the reaction. The reaction was stirred for 30 min and solvent and reagent removed in vacuo. Methylene chloride (1 mL) was added to the residue, followed by 4-(benzyloxy)-2-(trifluoromethyl)benzoic hydrazide (8-B) (141 mg, 0.46 mmol) and triethylamine (0.07 mL, 0.46 mmol). The reaction was stirred at room temperature overnight to afford intermediate 8-C, N′-[4-(benzyloxy)-2-(trifluoromethyl)benzoyl]-4-phenylbicyclo[2.2.2]octane-1-carbohydrazide, which was not isolated. To the crude product (8-C) were then added 2-chloro-1,3-dimethylimidazolinium chloride (257 mg, 1.52 mmol), more triethylamine (0.42 mL, 3.04 mmol), and methylene chloride (2 mL). The reaction was stirred at room temperature for 4 h. The reaction mixture was then diluted with methylene chloride (30 mL) and washed with water (30 mL) two times and with brine (30 mL) once. The combined aqueous layers were extracted with methylene chloride (25 mL) once. The combined organic layers were dried (MgSO4) and the solvent removed in vacuo. The residue was chromatographed on silica with 10% ethyl acetate in hexanes as eluant to give 2-[4-(benzyloxy)-2-(trifluoromethyl)pheny ]-5-(4-phenylbicyclo[2.2.2]oct-1-yl)-1,3,4-oxadiazole (8-D). MS: m/z 505 (M+1).

Workup

  1. customthe reaction
  2. customsolvent and reagent removed in vacuo
  3. additionMethylene chloride (1 mL) was added to the residue
  4. stirringThe reaction was stirred at room temperature overnight

Sources & evidence

ORD record
ord-ff54322d153a4dc4b467848c1630342a
Source dataset
uspto-grants-2009_03
Patent number
US07504402B2

Reaction notes

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