Sodium Dithionite → HCID 11609721, compound

HRID 646872Notes

Reaction equation

HRID 646872 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[N:9]([C:12]1[CH:13]=[CH:14][C:15]([N+:24]([O-])=O)=[C:16]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:17]=1)=[N+:10]=[N-:11].[C:27]([C:29]1[O:33][C:32]([C:34](Cl)=[O:35])=[CH:31][CH:30]=1)#[N:28].CCN(C(C)C)C(C)C>O.C1COCC1.[Cl-].[Na+].O>[N:9]([C:12]1[CH:13]=[CH:14][C:15]([NH:24][C:34]([C:32]2[O:33][C:29]([C:27]#[N:28])=[CH:30][CH:31]=2)=[O:35])=[C:16]([N:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[CH:17]=1)=[N+:10]=[N-:11]

Participants

8

Reactant 4

HCID 24489Sodium DithioniteHCID 81531DiisopropylethylamineHCID 202590395-Cyano-2-furoyl chlorideHCID 86241578HCID 86241578, compound

Product 1

HCID 11609721HCID 11609721, compoundYield 12%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of sodium hydrosulfite (936 mg, 5.30 mmol) in 8 mL of water was added 1-(5-azido-2-nitro-phenyl)-piperidine (133 mg, 0.530 mmol, as prepared in the previous step) in 4 mL of THF dropwise. After 25 min the reaction was poured into 50 mL of brine, extracted with EtOAc (3×30 mL), dried (Na2SO4), and concentrated in vacuo. The crude product was then allowed to react in a manner similar to Example 4, step (c), with 5-cyano-furan-2-carbonyl chloride (31 mg, 0.20 mmol) in the presence of DIEA (203 μL, 1.16 mmol) to afford 8 mg (12%) of the title compound as an amber solid. 1H-NMR (CDCl3; 400 MHz): δ 9.58 (s, 1H), 8.44 (d, 1H, J=7.8 Hz), 7.22-7.30 (m, 2H), 6.81-6.89 (m, 2H), 2.81-2.86 (m, 4H), 1.79-1.82 (m, 4H), 1.62-1.65 (m, 2H); Mass spectrum (ESI, m/z): Calcd. for C17H16N6O2, 337.1 (M+H), found 337.0.

Workup

  1. extractionextracted with EtOAc (3×30 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a0f1cd978a744dd99deaf2b15fa67391
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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