Triethylamine → HCID 178433046, compound

HRID 1488130Notes

Reaction equation

HRID 1488130 reaction equation
[I:1][C:2]1[NH:6][C:5]([C:7]([OH:9])=O)=[N:4][C:3]=1[CH3:10].[CH3:11][N:12](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)[CH3:13].F[P-](F)(F)(F)(F)F.Cl.CNC.C(N(CC)CC)C>CN(C)C=O.CCOC(C)=O>[I:1][C:2]1[NH:6][C:5]([C:7]([N:12]([CH3:13])[CH3:11])=[O:9])=[N:4][C:3]=1[CH3:10]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 178433053HCID 178433053, compound2×

Product 1

HCID 178433046HCID 178433046, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into a 100-mL round-bottom flask, was placed a solution of 5-iodo-4-methyl-1H-imidazole-2-carboxylic acid (compound 239.3, 200 mg, 0.79 mmol) in N,N-dimethylformamide (4 mL). HBTU (602 mg, 1.59 mmol), dimethylamine hydrochloride (96 mg, 1.18 mmol) and triethylamine (552 μL, 3.96 mmol) were added to the reaction. The reaction mixture was stirred for 3 h at room temperature, then diluted with 50 mL of EtOAc. The organic layer was washed with 2×20 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. This resulted in 150 mg (68%) of the title compound as yellow oil.

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. washThe organic layer was washed with 2×20 mL of brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8dc60680387f4adeae212d9c522c452f
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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