Triethylamine → HCID 86603474, compound

HRID 2378089Notes

Reaction equation

HRID 2378089 reaction equation
NC1[C:3]([O:17]C)=[C:4](NS(C)(=O)=O)[CH:5]=[C:6]([C:8](C)(C)C)C=1.C([N:21](CC)CC)C.O[N:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2N=N1>CN(C=O)C.CCOC(C)=O>[CH:6]([C:5]1[C:30]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[NH:27][C:4]=1[C:3]([NH2:21])=[O:17])=[CH2:8]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 10214710N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide

Product 1

HCID 86603474HCID 86603474, compoundYield 508.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the above carboxylic acid (1.6 g, 8.2 mmol) in DMF (80 mL) was added N-(3-amino-5-tert-butyl-2-methoxy-phenyl)-methanesulfonamide (2.21 g, 8.14 mmol.), O-(7-azobenzotriazol-1-yl)-N,N,N′,N′-tetrauroniumhexafluorophosphate (HATU, 3.15 g, 8.260 mmol), 2.56 mL of triethylamine (2.56 mL, 18.4 mmol), and 1-hydroxybenzotriazole (HOAT, 307.4 mg, 2.240 mmol). The resulting mixture was stirred at room temperature overnight. The reaction mixture was then diluted with EtOAc, washed with water, dried with sodium sulfate and concentrated. The crude product was purified by silica gel chromatography to afford 2.12 g (56.8%) of the desired ethenylindole amide.

Workup

  1. washwashed with water
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-4ac3c4711df745aeb96a6838a67c7fa0
Source dataset
uspto-grants-2008_12
Patent number
US07470692B2

Reaction notes

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