Dimethylformamide → 3-Chloro-N-(1-(2-(3,3-dimethylbutanamido)ethyl)-1H-tetrazol-5-yl)benzamide

HRID 872255Notes

Reaction equation

HRID 872255 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][C:8]1[N:12]([CH2:13][CH2:14]C)[N:11]=[N:10][N:9]=1)=[O:6].[C:19](OC(=O)NCCBr)([CH3:22])([CH3:21])[CH3:20].[CH3:30][CH2:31][N:32](CC)CC.CN(C=[O:41])C>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][C:8]1[N:12]([CH2:13][CH2:14][NH:32][C:31](=[O:41])[CH2:30][C:19]([CH3:20])([CH3:21])[CH3:22])[N:11]=[N:10][N:9]=1)=[O:6]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 9657943-Chloro-N-(1-propyl-1H-tetrazol-5-yl)benzamideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamate

Product 1

HCID 904081113-Chloro-N-(1-(2-(3,3-dimethylbutanamido)ethyl)-1H-tetrazol-5-yl)benzamideYield 42%

Procedure

Compound (A) (250 mg; 1.12 mmol), Compound (B) (250 mg; 1.12 mmol) and 340 mg (3.36 mmol) of Et3N were added to a round bottomed flask containing 15 ml of DMF and refluxed overnight (about 18 hours). The reaction mixture was evaporated to dryness under reduced pressure and 20 ml of H2O added. This aqueous phase was extracted with CH2Cl2 (3×30 ml) and the organic layers combined, dried over MgSO4 and further concentrated. The crude product obtained was purified over silica gel and eluted with CHCl3. To provide a brown oil in 42% yield.

Workup

  1. temperaturerefluxed overnight (about 18 hours)
  2. customThe reaction mixture was evaporated to dryness under reduced pressure and 20 ml of H2O
  3. additionadded
  4. extractionThis aqueous phase was extracted with CH2Cl2 (3×30 ml)
  5. dry with materialdried over MgSO4
  6. concentrationfurther concentrated

Sources & evidence

ORD record
ord-bc4b7b4ef05e4d15a73cab3ba4067b96
Source dataset
uspto-grants-2015_03
Patent number
US08975288B2

Reaction notes

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