Sodium Azide → HCID 59577514, compound

HRID 1947507Notes

Reaction equation

HRID 1947507 reaction equation
Cl[CH2:2][C:3]1[C:7]2[CH:8]=[CH:9][C:10]([O:12][C:13]3[S:14][C:15]4[C:16]([N:21]=3)=[N:17][CH:18]=[CH:19][CH:20]=4)=[CH:11][C:6]=2[O:5][CH:4]=1.[N-:22]=[N+:23]=[N-:24].[Na+]>CN(C=O)C>[N:22]([CH2:2][C:3]1[C:7]2[CH:8]=[CH:9][C:10]([O:12][C:13]3[S:14][C:15]4[C:16]([N:21]=3)=[N:17][CH:18]=[CH:19][CH:20]=4)=[CH:11][C:6]=2[O:5][CH:4]=1)=[N+:23]=[N-:24]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 59577637HCID 59577637, compound

Product 1

HCID 59577514HCID 59577514, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3-chloromethyl-benzofuran-6-yloxy)-thiazolo[4,5-b]pyridine (2.7 g, 8.5 mmol) in DMF (42 mL) at 0° C. was added sodium azide (0.61 g, 9.3 mmol). The mixture was stirred at (rt, 3 h), partitioned between ethyl acetate and brine, dried, filtered and concentrated. Upon addition of ethyl acetate and hexanes, precipitate was formed and filtered. Concentration and purification by silica gel flash chromatography using ethyl acetate/hexanes provided a solid that was combined with the previously filtered precipitate to provide the title compound (1.8 g, 65%). MS (ESI): mass calcd. for C15H9N5O2S, 323.05; m/z found, 324.0 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.57 (dd, J=4.8, 1.6, 1H), 8.09-7.95 (m, 1H), 7.74-7.64 (m, 3H), 7.36 (dd, J=8.5, 2.1, 1H), 7.22 (dd, J=7.9, 4.8, 1H), 4.50 (s, 2H).

Workup

  1. custompartitioned between ethyl acetate and brine
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionUpon addition of ethyl acetate and hexanes
  6. customprecipitate was formed
  7. filtrationfiltered
  8. concentrationConcentration and purification by silica gel flash chromatography
  9. customprovided a solid

Sources & evidence

ORD record
ord-2a5bb938e1a64581856696ab70bd876f
Source dataset
uspto-grants-2013_03
Patent number
US08399465B2

Reaction notes

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