Triethylamine → HCID 131718983, compound

HRID 1654755Notes

Reaction equation

HRID 1654755 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][CH2:12][CH2:13][CH:14]1[O:18][CH:17]2[O:19][CH:20](C3C=CC(F)=CC=3)[CH2:21][CH:16]2[CH2:15]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[N+:8]([C:3]1[CH:4]=[N:5][CH:6]=[CH:7][C:2]=1[NH:11][CH2:12][CH2:13][CH:14]1[O:18][CH:17]2[O:19][CH2:20][CH2:21][CH:16]2[CH2:15]1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27357814-Chloro-3-nitropyridineHCID 20076816HCID 20076816, compound

Product 1

HCID 131718983HCID 131718983, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4Chloro-3-nitropyridine (160 mg, 1.0 mmol) is added to a stirred solution of 5-(2-aminoethyl)-2-(4-fluorophenyl)hexahydrofuro[2,3-b]furan (200 mg, 0.8 mmol) and triethylamine (1.0 ml) in chloroform (15 ml) at ambient temperature. The reaction mixture is stirred overnight, then washed with water, dried over anhydrous magnesium sulphate, filtered and the solvent removed under reduced pressure to leave an orange oil. This is purified by chromatography over silica (1:1 ethyl acetate/hexane) to give 2-(4-fluorophenyl)-5-(2-(N-3-nitropyrid-4-ylaminoethyl)hexahydrofuro[2,3-b]furan (175 mg, 59%) as a yellow amorphous solid.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous magnesium sulphate
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customto leave an orange oil
  6. customThis is purified by chromatography over silica (1:1 ethyl acetate/hexane)

Sources & evidence

ORD record
ord-02d54aed9bfc4e769c387390c9351bbe
Source dataset
uspto-grants-1995_04
Patent number
US05409937

Reaction notes

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