Azido(trimethyl)stannane → 1-(1-Ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid [(S)-3-methyl-1-(1H-tetrazol-5-ylmethyl)-butyl]-amide

HRID 1750174Notes

Reaction equation

HRID 1750174 reaction equation
[C:1]([CH2:3][C@@H:4]([NH:9][C:10]([C:12]1[CH:31]=[CH:30][C:15]2[N:16]([CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[C:17]([CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)=[N:18][C:14]=2[CH:13]=1)=[O:11])[CH2:5][CH:6]([CH3:8])[CH3:7])#[N:2].[N:32]([Sn](C)(C)C)=[N+:33]=[N-:34]>C1(C)C=CC=CC=1.C(=O)(O)[O-].[Na+]>[CH3:7][CH:6]([CH3:8])[CH2:5][C@H:4]([NH:9][C:10]([C:12]1[CH:31]=[CH:30][C:15]2[N:16]([CH:25]([CH2:28][CH3:29])[CH2:26][CH3:27])[C:17]([CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)=[N:18][C:14]=2[CH:13]=1)=[O:11])[CH2:3][C:1]1[NH:34][N:33]=[N:32][N:2]=1

Participants

5

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 867143851-(1-Ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid ((S)-1-cyanomethyl-3-methyl-butyl)-amide

Product 1

HCID 1784460871-(1-Ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid [(S)-3-methyl-1-(1H-tetrazol-5-ylmethyl)-butyl]-amideYield 42%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

218 mg of 1-(1-ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid ((S)-1-cyanomethyl-3-methyl-butyl)-amide and 124 mg of azidotrimethyltin in 10 ml of dry toluene were heated under Argon for 48 h. The precipitated crude product was isolated by suction and then dissolved in 10% aqueous sodium bicarbonate solution and filtered with addition of charcoal. The pH of the filtrated was adjusted to 5, and the precipitated product was isolated by suction, washed with water and dried in vacuo to obtain 100 mg (42%) of 1-(1-Ethyl-propyl)-2-thiophen-2-ylmethyl-1H-benzoimidazole-5-carboxylic acid [(S)-3-methyl-1-(1H-tetrazol-5-ylmethyl)-butyl]-amide.

Workup

  1. customThe precipitated crude product
  2. customwas isolated by suction
  3. filtrationfiltered with addition of charcoal
  4. customthe precipitated product was isolated by suction
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-4dad43cd23a74f7fa590439de06c5be4
Source dataset
uspto-grants-2015_10
Patent number
US09156796B2

Reaction notes

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