Diisopropylethylamine → (2-(Pyrid-4-yl)-1h-benzimidazole-4-carbonyl)-(l)-leucine methyl ester

HRID 278031Notes

Reaction equation

HRID 278031 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([OH:18])=O)[C:9]=3[N:8]=2)=[CH:3][CH:2]=1.[B-](F)(F)(F)F.C[CH2:25][O:26][C:27]([C:29]([C:39]#N)=[N:30]OC(N(C)C)=[N+](C)C)=[O:28].[CH:41](N(C(C)C)CC)([CH3:43])[CH3:42]>CN(C=O)C>[CH3:25][O:26][C:27](=[O:28])[C@H:29]([CH2:39][CH:41]([CH3:43])[CH3:42])[NH:30][C:16]([C:15]1[C:9]2[N:8]=[C:7]([C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[NH:11][C:10]=2[CH:12]=[CH:13][CH:14]=1)=[O:18]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 112071702-Pyridin-4-yl-3H-benzoimidazole-4-carboxylic acid

Product 1

HCID 15480893(2-(Pyrid-4-yl)-1h-benzimidazole-4-carbonyl)-(l)-leucine methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

120 mg (0.5 mmol) of 2-(pyrid-4-yl)-1H-benzimidazole-4-carboxylic acid (1d) and 84 mg (0.5 mmol) of H-(L)-leucine methyl ester were dissolved in 5 ml of DMF. 164 mg (0.5 mmol) of TOTU and 0.086 ml of diisopropylethylamine were added and the mixture was stirred at RT for 3 h. The precipitate was filtered off and the filtrate was concentrated. The residue was dissolved in ethyl acetate, the solution was washed with water, and the organic phase was dried using anhydrous sodium sulfate and concentrated. Yield: 180 mg (98%).

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed with water
  5. customthe organic phase was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-184fe2b0b5f24a8d8c53a2db5518b886
Source dataset
uspto-grants-2002_03
Patent number
US06358978B1

Reaction notes

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