Tetrahydrofuran → HCID 178442643, compound

HRID 717614Notes

Reaction equation

HRID 717614 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-f93b29ef0bf14bdbb36fc9cc1eea3392
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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