1,8-Diazabicyclo(5.4.0)undec-7-ene → (E)-2-(2-(5-Methyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)vinyl)-[1,2,4]triazolo[5,1-f][1,6]naphthyridine

HRID 1615656Notes

Reaction equation

HRID 1615656 reaction equation
[N:1]1[C:2]([CH:14]=O)=[N:3][N:4]2[CH:13]=[CH:12][C:11]3[N:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]=12.[Cl-].[CH3:17][C:18]1[N:23]2[N:24]=[C:25]([CH2:27][P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[N:26]=[C:22]2[CH:21]=[CH:20][CH:19]=1.C1CCN2C(=NCCC2)CC1>C1COCC1.C(Cl)Cl>[CH3:17][C:18]1[N:23]2[N:24]=[C:25](/[CH:27]=[CH:14]/[C:2]3[N:1]=[C:5]4[C:6]5[CH:7]=[CH:8][CH:9]=[N:10][C:11]=5[CH:12]=[CH:13][N:4]4[N:3]=3)[N:26]=[C:22]2[CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86667811[1,2,4]Triazolo[5,1-f][1,6]naphthyridine-2-carbaldehydeHCID 86667812((5-Methyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)methyl)triphenylphosphonium chloride

Product 1

HCID 68089402(E)-2-(2-(5-Methyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)vinyl)-[1,2,4]triazolo[5,1-f][1,6]naphthyridineYield 52%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [1,2,4]triazolo[5,1-f][1,6]naphthyridine-2-carbaldehyde (20 mg, 0.1 mmol) in THF (1 mL) was added a solution of ((5-methyl-[1,2,4]triazolo[1,5-a]pyridin-2-yl)methyl)triphenylphosphonium chloride (49 mg, 0.11 mmol) in DCM (3 mL), followed by the addition of DBU (45 mg, 0.3 mmol) at 0° C. under N2. The resulting mixture was stirred for 4 h at room temperature and diluted with DCM (15 mL). The mixture was washed with water (10 mL), brine (10 mL), dried over anhydrous Na2SO4, filtered and concentrated to give a crude residue, which was purified by prep. TLC to afford the title compound (17 mg, yield 52%). ESI MS: m/z 328 [M+H]+.

Workup

  1. washThe mixture was washed with water (10 mL), brine (10 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude residue, which
  6. customwas purified by prep

Sources & evidence

ORD record
ord-21e1fa0d36de4327935c09e3c20af2b4
Source dataset
uspto-grants-2014_07
Patent number
US08765760B2

Reaction notes

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