Azidotrimethylsilane → HCID 178419458, compound

HRID 1806123Notes

Reaction equation

HRID 1806123 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Br:19][C:20]1[CH:21]=[C:22]([O:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:23]([NH:26][C:27]2[S:28][CH:29]=[C:30]([CH2:32][CH2:33][C:34]#[N:35])[N:31]=2)=[N:24][CH:25]=1.[Si]([N:47]=[N+:48]=[N-:49])(C)(C)C>C(Cl)Cl>[NH:47]1[C:34]([CH2:33][CH2:32][C:30]2[N:31]=[C:27]([NH:26][C:23]3[C:22]([O:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[CH:21][C:20]([Br:19])=[CH:25][N:24]=3)[S:28][CH:29]=2)=[N:35][N:49]=[N:48]1

Participants

5

Reactant 3

HCID 78378AzidotrimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 57742723HCID 57742723, compound

Product 1

HCID 178419458HCID 178419458, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

To a nitrogen purged vial was added TBAF (0.249 mL, 0.249 mmol), 3-(2-(5-bromo-3-phenoxypyridin-2-ylamino)thiazol-4-yl)propanenitrile (0.200 g, 0.498 mmol) (Example 320), and TMSN3 (0.0992 mL, 0.748 mmol) were added, and the reaction was stirred at 120° C. for 24 Hr. The crude reaction mixture was dissolved in CH2Cl2 and washed with aqueous sodium bicarbonate solution. The organic layer was concentrated to a residue that was purified on silica gel by eluting with 7% MeOH/CH2Cl2 and further purified by triturating in refluxing EtOAc to give the title compound (0.128 g, 57.8% yield). 1H NMR (d6 DMSO) δ 3.03 (t, J=7.5 Hz, 2H), 3.25 (t, J=7.6 Hz, 2H), 6.70 (s, 1H), 7.13 (d, J=8.0 Hz, 2H), 7.22 (t, J=7.3 Hz, 1H), 7.38 (d, J=2.0 Hz, 1H), 7.45 (t, J=7.9 Hz, 2H), 8.22 (d, J=2.2 Hz, 1H), 11.01 (s, 1H).

Workup

  1. additionwere added
  2. customThe crude reaction mixture
  3. washwashed with aqueous sodium bicarbonate solution
  4. concentrationThe organic layer was concentrated to a residue that
  5. customwas purified on silica gel
  6. washby eluting with 7% MeOH/CH2Cl2
  7. customfurther purified
  8. customby triturating
  9. temperaturein refluxing EtOAc

Sources & evidence

ORD record
ord-04152a1233a347c3b62df4b2ebdec0a1
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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