Dibutyltin oxide → {5-[2-[(N-Benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-(2H-tetrazol-5-yl)-phenyl]-pyridin-3-yl}-acetic acid

HRID 554594Notes

Reaction equation

HRID 554594 reaction equation
[CH2:1]([O:3][C:4](=[O:34])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][C:13]=2[CH2:20][N:21]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]([CH:24]2[CH2:26][CH2:25]2)=[O:23])[CH:11]=1)[CH3:2].C([Sn](=O)CCCC)CCC.[N:45]([Si](C)(C)C)=[N+:46]=[N-:47]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:34])[CH2:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:45]=[N:46][NH:47][N:19]=3)=[CH:14][C:13]=2[CH2:20][N:21]([CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:22]([CH:24]2[CH2:26][CH2:25]2)=[O:23])[CH:11]=1)[CH3:2].[CH2:27]([N:21]([CH2:20][C:13]1[CH:14]=[C:15]([C:18]2[N:45]=[N:46][NH:47][N:19]=2)[CH:16]=[CH:17][C:12]=1[C:10]1[CH:11]=[C:6]([CH2:5][C:4]([OH:3])=[O:34])[CH:7]=[N:8][CH:9]=1)[C:22]([CH:24]1[CH2:25][CH2:26]1)=[O:23])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 67212964(5-{2-[(Benzyl-cyclopropanecarbonyl-amino)-methyl]-4-cyano-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

Product 2

HCID 45138332{5-[2-[(N-Benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-(2H-tetrazol-5-yl)-phenyl]-pyridin-3-yl}-acetic acidHCID 58565080{5-[2-[(N-benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-(2H-tetrazol-5-yl)-phenyl]-pyridin-3-yl}-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

(5-{2-[(N-Benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-cyano-phenyl}-pyridin-3-yl)-acetic acid ethyl ester (0.253 g, 0.56 mmol) was dissolved in toluene (10 mL). Dibutyltin oxide (0.014 g, 0.06 mmol) was added, followed by azidotrimethylsilane (0.09 mL, 0.67 mmol), and the reaction was stirred at 80° C. for 5 hours, and at 100° C. overnight. The mixture was quenched with H2O and extracted with EtOAc. The combined organic layers were concentrated and purified by preparative HPLC to give {5-[2-[(N-benzyl-N-cyclopropanecarbonyl-amino)-methyl]-4-(2H-tetrazol-5-yl)-phenyl]-pyridin-3-yl}-acetic acid ethyl ester the title compound.

Workup

  1. customat 100° C.
  2. customovernight
  3. customThe mixture was quenched with H2O
  4. extractionextracted with EtOAc
  5. concentrationThe combined organic layers were concentrated
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-1905ee7ed9154e29b9343731b18b9e54
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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