Triethylamine → HCID 59574484, compound

HRID 2092109Notes

Reaction equation

HRID 2092109 reaction equation
[Cl:1][C:2]1[C:3](=[O:23])[N:4]([CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:14][CH:13]=2)=[O:11])[N:5]=[CH:6][C:7]=1Cl.[CH2:24]1[CH:31]2[C:27]3([NH2:33])[CH2:28][CH:29]([CH2:32][CH:25]1[CH2:26]3)[CH2:30]2.C(N(CC)CC)C.[Cl-].[NH4+]>CN(C)C(=O)C>[Cl:1][C:2]1[C:3](=[O:23])[N:4]([CH2:9][C:10]([C:12]2[CH:17]=[CH:16][C:15]([N:18]([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:14][CH:13]=2)=[O:11])[N:5]=[CH:6][C:7]=1[NH:33][C:27]12[CH2:28][CH:29]3[CH2:32][CH:25]([CH2:24][CH:31]1[CH2:30]3)[CH2:26]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2794246HCID 2794246, compoundHCID 59574171HCID 59574171, compound

Product 1

HCID 59574484HCID 59574484, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

4,5-Dichloro-2-{2-[4-(diethylamino)phenyl]-2-oxoethyl}pyridazin-3(2H)-one (30 mg, 0.0846 mmol), hexahydro-2,5-methanopentalen-3a(1H)-amine (22 mg, 0.126 mmol) and triethylamine (59 μL, 0.423 mmol) were stirred in N,N-dimethylacetamide (1 mL) at 90° C. for 3 days. After completion of the reaction, the reaction solution was mixed with aqueous ammonium chloride and extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1) to give the desired product (7 mg, 17% yield).

Workup

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-5c31bf45506047158f41abdd90ecf857
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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