Tributyltin azide → HCID 178446083, compound

HRID 2355246Notes

Reaction equation

HRID 2355246 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][C:14]([NH:17][CH2:18][C@@H:19]([C:21]1[CH:22]=[C:23]([NH:27][S:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)(=[O:30])=[O:29])[CH:24]=[CH:25][CH:26]=1)[OH:20])([CH3:16])[CH3:15])[CH:7]=[CH:6]2)#[N:2].C([Sn]([N:50]=[N+:51]=[N-:52])(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[CH3:16][C:14]([NH:17][CH2:18][C@@H:19]([C:21]1[CH:22]=[C:23]([NH:27][S:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:30])=[O:29])[CH:24]=[CH:25][CH:26]=1)[OH:20])([CH3:15])[CH2:13][CH2:12][N:8]1[C:9]2[C:5](=[CH:4][C:3]([C:1]3[NH:52][N:51]=[N:50][N:2]=3)=[CH:11][CH:10]=2)[CH:6]=[CH:7]1

Participants

4

Reactant 2

HCID 4984872Tributyltin azide2×HCID 58875107HCID 58875107, compound

Product 1

HCID 178446083HCID 178446083, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

150 mg (0.30 mmol) N-(3-{(R)-2-[3-(5-cyano-indol-1-yl)-1,1-dimethyl-propylamino]-1-hydroxy-ethyl}-phenyl)-benzenesulphonamide (Example 1) are dissolved in 5 ml of toluene and combined with 98 μl (0.36 mmol) tributyltin azide. Then the reaction solution is refluxed for 18 hours. Another 164 μl (0.6 mmol) tributyltin azide are added. The mixture is refluxed for a further 36 hours. Then the solvent is eliminated in vacuo and the residue is chromatographed on silica gel (DCM/methanol/NH4OH=100:0:0→70:30:0.3).

Workup

  1. temperatureThen the reaction solution is refluxed for 18 hours
  2. temperatureThe mixture is refluxed for a further 36 hours
  3. customthe residue is chromatographed on silica gel (DCM/methanol/NH4OH=100:0:0→70:30:0.3)

Sources & evidence

ORD record
ord-ab7a7a36c3024c4c8cf14e4e128badcf
Source dataset
uspto-grants-2010_07
Patent number
US07754756B2

Reaction notes

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