Tributyltin azide → HCID 178521906, compound

HRID 133700

Reaction equation

HRID 133700 reaction equation
C([Sn]([N:14]=[N+:15]=[N-:16])(CCCC)CCCC)CCC.[CH2:17]([O:24][C:25]1[CH:26]=[C:27]([CH:39]=[C:40]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)[CH:41]=1)[C:28]([NH:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][N:32]=1)=[O:29])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1(C)C=CC=CC=1>[CH2:43]([O:42][C:40]1[CH:39]=[C:27]([CH:26]=[C:25]([O:24][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:41]=1)[C:28]([NH:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]2[NH:16][N:15]=[N:14][N:38]=2)=[CH:33][N:32]=1)=[O:29])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

4

Reactant 2

HCID 4984872Tributyltin azideHCID 230729493,5-bis(benzyloxy)-N-(5-cyanopyridin-2-yl)benzamide

Product 1

HCID 178521906HCID 178521906, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Tributyltin azide (156 μL, 0.57 mmol) was added to a suspension of 3,5-bis(benzyloxy)-N-(5-cyanopyridin-2-yl)benzamide (180 mg, 0.41 mmol) in toluene (3 mL). The mixture was heated at reflux for 16 hours. The suspension was cooled and partitioned between ethyl acetate and hydrochloric acid (1M). The organic layer was concentrated in vacuo and the residue was purified by MPLC on silica MPLC (eluting with 1% methanol/DCM to 15% methanol/DCM). The tetrazole was obtained as a colourless solid (113 mg, 57%). 1H NMR δ (d6-DMSO): 5.19 (4H, s); 6.88 (1H, s); 7.26-7.48 (12H, m); 8.40 (1H, d); 8.46 (1H, dd); 9.04 (1H, s); 11.13 (1H, br s); m/z (LCMS; ESI+) 479 (MH+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 hours
  3. temperatureThe suspension was cooled
  4. custompartitioned between ethyl acetate and hydrochloric acid (1M)
  5. concentrationThe organic layer was concentrated in vacuo
  6. customthe residue was purified by MPLC on silica MPLC (eluting with 1% methanol/DCM to 15% methanol/DCM)

Sources & evidence

ORD record
ord-5cc050a25abf4deb850b771018e040a0
Source dataset
uspto-grants-2008_06
Patent number
US07390908B2

Linked notes

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