Sodium Azide → HCID 70981929, compound

HRID 716186Notes

Reaction equation

HRID 716186 reaction equation
Cl[CH2:2][C:3]1[N:8]=[N:7][C:6]([C:9]2[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=2[F:20])[C:12]([N:14]([CH3:16])[CH3:15])=[O:13])=[CH:5][CH:4]=1.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C=O)C>[N:21]([CH2:2][C:3]1[N:8]=[N:7][C:6]([C:9]2[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=2[F:20])[C:12]([N:14]([CH3:16])[CH3:15])=[O:13])=[CH:5][CH:4]=1)=[N+:22]=[N-:23]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 89158211HCID 89158211, compound

Product 1

HCID 70981929HCID 70981929, compoundYield 71.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(6-(Chloromethyl)pyridazin-3-yl)-4-fluoro-N,N-dimethylbenzamide (470 mg, 1.60 mmol) was treated with NaN3 (312 mg, 4.80 mmol) and DMF (5 mL) and stirred at RT for 15 h. The reaction mixture was extracted with EtOAc and the organic layer was washed with water and brine (2×30 mL), dried over MgSO4, filtered and concentrated. Purification of the crude material by silica gel chromatography (30-100% EtOAc in hexanes) afforded 3-(6-(azidomethyl)pyridazin-3-yl)-4-fluoro-N,N-dimethylbenzamide (341 mg, 1.14 mmol, 71.0% yield) as a clear colorless film. MS (ESI, pos. ion) m/z: 301.1 (M+1). 1H NMR (400 MHz, CDCl3) δ ppm 8.29 (1 H, dd, J=7.3, 2.1 Hz), 8.02 (1 H, dd, J=8.8, 1.6 Hz), 7.57-7.69 (2 H, m), 7.22-7.31 (1 H, m), 4.81 (2 H, s), 3.08 (3 H, s), 3.13 (3 H, s). 19F NMR (376 MHz, CDCl3) δ ppm −115.30 (1F, s).

Workup

  1. extractionThe reaction mixture was extracted with EtOAc
  2. washthe organic layer was washed with water and brine (2×30 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the crude material by silica gel chromatography (30-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-7a840e14069a493896b22cc202f75509
Source dataset
uspto-grants-2015_11
Patent number
US09187486B2

Reaction notes

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