Chlorotrimethylsilane → 2-(3-Ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl) [1,3]thiazolo[5',4': 3,4]benzo[c]isoxazol-8-yl cyanide

HRID 9169Notes

Reaction equation

HRID 9169 reaction equation
[CH2:1]([N:3]1[CH2:8][N:7]([CH3:9])[CH2:6][N:5]([C:10]2[S:11][C:12]3[C:18]([CH2:19][C:20]#[N:21])=[C:17]([N+:22]([O-])=[O:23])[CH:16]=[CH:15][C:13]=3[N:14]=2)[C:4]1=[O:25])[CH3:2].C(N(CC)CC)C.C[Si](Cl)(C)C>CN(C)C=O>[CH2:1]([N:3]1[CH2:8][N:7]([CH3:9])[CH2:6][N:5]([C:10]2[S:11][C:12]3[C:18]4[C:17](=[N:22][O:23][C:19]=4[C:20]#[N:21])[CH:16]=[CH:15][C:13]=3[N:14]=2)[C:4]1=[O:25])[CH3:2]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 21985644HCID 21985644, compound

Product 1

HCID 701226262-(3-Ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl) [1,3]thiazolo[5',4': 3,4]benzo[c]isoxazol-8-yl cyanide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.2 g of [2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-6-nitro-1,3-benzothiazol-7-yl]methyl cyanide was charged into about 2 ml dimethylformamide. About 15 equivalents of triethylamine were then added followed by about 15 equivalents of trimethylsilyl chloride. The solution was stirred at room temperature for about 4–20 hours. The reaction was quenched by pouring into dilute aqueous hydrochloric acid then extracted well with ethyl acetate. The combined organics were back extracted with dilute sodium bicarbonate then dried over magnesium sulfate and concentrated. The dark oil was further purified by preparative HPLC to yield 2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl) [1,3]thiazolo[5′,4′: 3,4]benzo[c]isoxazol-8-yl cyanide.

Workup

  1. customThe reaction was quenched
  2. additionby pouring into dilute aqueous hydrochloric acid
  3. extractionthen extracted well with ethyl acetate
  4. extractionThe combined organics were back extracted with dilute sodium bicarbonate
  5. dry with materialthen dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe dark oil was further purified by preparative HPLC

Sources & evidence

ORD record
ord-169aea1b049e4e39bff2a3959b722b9c
Source dataset
uspto-grants-2006_08
Patent number
US07091227B2

Reaction notes

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