Dimethylformamide → (2-(Pyrid-4-yl)-1H-benzimidazole-4-carbonyl)-(L)-valinamide

HRID 278032

Reaction equation

HRID 278032 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.CCO[C:27]([C:29]([C:39]#[N:40])=NOC(N(C)C)=[N+](C)C)=O.[CH:41](N(C(C)C)CC)(C)C.C[N:51]([CH:53]=[O:54])C>>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([NH:40][C@H:39]([C:53]([NH2:51])=[O:54])[CH:29]([CH3:41])[CH3:27])=[O:18])[C:9]=3[N:8]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 112071702-Pyridin-4-yl-3H-benzoimidazole-4-carboxylic acid

Product 1

HCID 11416447(2-(Pyrid-4-yl)-1H-benzimidazole-4-carbonyl)-(L)-valinamide

Procedure

120 mg (0.5 mmol) of 2-(pyrid-4-yl)-1H-benzimidazole-4-carboxylic acid (1d) and 76.4 mg (0.5 mmol) of H-(L)-valinamide 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 saturated sodium chloride solution, and the organic phase was dried using anhydride sodium sulfate and concentrated. Yield: 168 mg (99%). (M+H)+=338.2 (Cl+).

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 saturated sodium chloride solution
  5. customthe organic phase was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cc209c226de84ecb942c3b52c5f48169
Source dataset
uspto-grants-2002_03
Patent number
US06358978B1

Linked notes

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