Sodium Azide → HCID 178514599, compound

HRID 2240077Notes

Reaction equation

HRID 2240077 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[C:7]([S:14]([C:17]1[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[N:8][NH:9]2.[N-:27]=[N+:28]=[N-:29].[Na+]>CS(C)=O.O>[N:27]([CH2:2][CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[C:7]([S:14]([C:17]1[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[N:8][NH:9]2)=[N+:28]=[N-:29]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 178527273HCID 178527273, compound

Product 1

HCID 178514599HCID 178514599, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(2-chloro-ethoxy)-3-(naphthalene-1-sulfonyl)-1-H-indazole (0.2 g, 0.5 mmoles) and sodium azide (0.04 g, 0.62 mmoles) in DMSO (2 mL) was stirred together in a round bottom flask under nitrogen at 90° C. for 3 hours. Reaction mixture was cooled to room temperature, diluted with water, extracted with EtOAC, washed with water (2×), brine (1×), dried over Na2SO4, and concentrated under vacuum. Crude compound was purified by normal phase HPLC using as eluent 40% EtOAc/hexane to afford the title compound as an off white solid (0.17 g, 0.45 mmoles).

Workup

  1. customReaction mixture
  2. temperaturewas cooled to room temperature
  3. extractionextracted with EtOAC
  4. washwashed with water (2×), brine (1×)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customCrude compound was purified by normal phase HPLC

Sources & evidence

ORD record
ord-53cc68186bbd4586a4dc98071122ff67
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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