Sodium Azide → HCID 58851677, compound

HRID 1696487Notes

Reaction equation

HRID 1696487 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([NH2:10])[N:7]([C:11]2[CH:20]=[C:19]([CH2:21]Cl)[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[N-:23]=[N+:24]=[N-:25].[Na+]>CN(C=O)C>[N:23]([CH2:21][C:19]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[C:11]([N:7]2[C:8]([NH2:10])=[CH:9][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[N:6]2)[CH:20]=1)=[N+:24]=[N-:25]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 67271754HCID 67271754, compound

Product 1

HCID 58851677HCID 58851677, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-t-butyl-1-[4-(chloromethyl)naphthalen-2-yl]-1H-pyrazol-5-amine (1.5 g, 4.8 mmol) in DMF (8 mL) was added NaN3 (325 mg, 5.0 mmol). The mixture was stirred at RT overnight, then poured into ice-H2O and extracted with EtOAc (3×100 mL). The combined organic extracts were washed with brine, dried (Na2SO4), filtered, concentrated and purified via column chromatography to afford 1-[4-(azidomethyl)naphthalen-2-yl]-3-t-butyl-1H-pyrazol-5-amine (1.35 g, 88% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.06 (m, 2H), 8.04 (m, 1H), 7.85 (s, 1H), 7.54-7.57 (m, 2H), 5.41 (s, 1H), 5.35 (brs, 2H), 4.96 (s, 2H), 1.21 (s, 9H); MS (ESI) m/z: 321 (M+H+).

Workup

  1. extractionextracted with EtOAc (3×100 mL)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified via column chromatography

Sources & evidence

ORD record
ord-c646db0468234b5dbf2e466b86e7b082
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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