Furfurylamine → 8-Bromo-[1,6]naphthyridine-2-carboxylic acid (furan-2-ylmethyl)-amide

HRID 1180566Notes

Reaction equation

HRID 1180566 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]([OH:14])=O)[CH:8]=[CH:7]2.[CH2:15]([NH2:21])[C:16]1[O:20][CH:19]=[CH:18][CH:17]=1.C(OP(C#N)(=O)OCC)C.C(N(CC)CC)C>CN(C=O)C>[O:20]1[CH:19]=[CH:18][CH:17]=[C:16]1[CH2:15][NH:21][C:12]([C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[C:2]([Br:1])[CH:3]=[N:4][CH:5]=2)[N:10]=1)=[O:14]

Participants

6

Reactant 4

HCID 3438FurfurylamineHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 27610508-bromo-1,6-naphthyridine-2-carboxylic Acid

Product 1

HCID 589795838-Bromo-[1,6]naphthyridine-2-carboxylic acid (furan-2-ylmethyl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Bromo-[1,6]naphthyridine-2-carboxylic acid (1) is stirred in DMF (20 mL) and furfurylamine (1 equiv.) is added. The reaction mixture is cooled to 0° C. (ice bath) and diethylcyanophosphonate (1 equiv.) is added followed immediately by triethylamine (2 equiv.). The reaction mixture is removed from the ice bath and stirred at room temperature for 26 hrs. The mixture is diluted with water (50 mL) and extracted with methylene chloride (3×50 mL). The combined organic layers are dried over sodium sulfate, filtered, and concentrated in vacuo to afford a tan solid, which is purified via silica gel chromatography (1:1; hexanes:EtOAc to 1:3.) LC/MS (M+H) 332.1.

Workup

  1. additionis added
  2. customThe reaction mixture is removed from the ice bath
  3. additionThe mixture is diluted with water (50 mL)
  4. extractionextracted with methylene chloride (3×50 mL)
  5. dry with materialThe combined organic layers are dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a tan solid, which
  9. customis purified via silica gel chromatography (1:1; hexanes:EtOAc to 1:3.) LC/MS (M+H) 332.1

Sources & evidence

ORD record
ord-8b901bc0fdbf42e89986f37c69b1e589
Source dataset
uspto-grants-2007_10
Patent number
US07282506B2

Reaction notes

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