Tetrahydrofuran → HCID 178442643, compound

HRID 2046030Notes

Reaction equation

HRID 2046030 reaction equation
[CH2:1]([C:9]1[CH:19]=[CH:18][C:12]([CH2:13][NH:14][CH2:15][C:16]#[N:17])=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[Si]([N:24]=[N+:25]=[N-:26])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1>CO>[NH:17]1[C:16]([CH2:15][NH:14][CH2:13][C:12]2[CH:18]=[CH:19][C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:10][CH:11]=2)=[N:26][N:25]=[N:24]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 78378AzidotrimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 46900483HCID 46900483, compound

Product 1

HCID 178442643HCID 178442643, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of the product of Step B (0.07 g; 0.271 mmol) and Me3SiN3 (0.36 ml; 2.71 mmol) and 1M TBAF in THF (0.27 ml; 0.271 mmol) was stirred at 75±5° C. for 8 h in sealed flask. After cooling to room temperature, the mixture was diluted to 1 ml with MeOH, refluxed for 30 min under N2 and left overnight in refrigerator. The precipitate formed was filtered off, washed with Et2O and dried to give a title compound (0.069 g; 84%) as colourless solid. 1H-NMR (CD3OD) 7.32 (d, 2H, J=8.0 Hz); 7.21 (d, 2H, J=8.0 Hz); 4.72 (s, CD3OH); 4.34 (s, 2H); 4.16 (s, 2H); 2.59 (t, 2H, J=7.76 Hz); 1.57 (t, 2H, J=7.19 Hz); 1.25 (m, 10H); 0.84 (t, 3H, J=6.93 Hz);

Workup

  1. temperatureAfter cooling to room temperature
  2. temperaturerefluxed for 30 min under N2
  3. waitleft overnight in refrigerator
  4. customThe precipitate formed
  5. filtrationwas filtered off
  6. washwashed with Et2O
  7. customdried

Sources & evidence

ORD record
ord-cb552640c0914f71999df613225284e6
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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