Triethylamine → HCID 18770630, compound

HRID 479501Notes

Reaction equation

HRID 479501 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][CH:9]([N:14]=[C:15]=[S:16])[C:10]([Cl:13])([Cl:12])[Cl:11])=[O:7])=[CH:4][CH:3]=1.[NH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH:9]([NH:14][C:15]([NH:19][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=2)=[S:16])[C:10]([Cl:12])([Cl:13])[Cl:11])=[O:7])=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 18770730HCID 18770730, compound

Product 1

HCID 18770630HCID 18770630, compoundYield 52.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 45A (239mg, 0.695 mmol) and 3-aminopyridine (65 mg, 0.69 mmol) in THF (4 mL) at ambient temperature was treated with triethylamine (1.66 mL, 1.18 mmol). The mixture was stirred for 3 hours, diluted with ethyl acetate (20 mL), and washed with water (2×10 mL) and brine (10 mL). The organic portion was dried (MgSO4), filtered, and concentrated to provide an oily residue which was purified by flash chromatography (elution with 5% ethanol/hexanes) to provide 158 mg of the desired product as an off-white solid.

Workup

  1. washwashed with water (2×10 mL) and brine (10 mL)
  2. dry with materialThe organic portion was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto provide an oily residue which
  6. customwas purified by flash chromatography (elution with 5% ethanol/hexanes)

Sources & evidence

ORD record
ord-6e244046cec44d90a459ed7dda71edc8
Source dataset
uspto-grants-2003_11
Patent number
US06645968B2

Reaction notes

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