Diisopropylamine → 2-pyridin-4-yl-1H-benzimidazole-5-carboxylic acid (1-[1,3,4]oxadiazol-2-yl-3-phenylpropyl)amide

HRID 278035Notes

Reaction equation

HRID 278035 reaction equation
[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[CH:6]([NH2:15])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[N:16]1[CH:21]=[CH:20][C:19]([C:22]2[NH:26][C:25]3[CH:27]=[CH:28][C:29]([C:31](O)=[O:32])=[CH:30][C:24]=3[N:23]=2)=[CH:18][CH:17]=1.[B-](F)(F)(F)F.CCOC(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.C(NC(C)C)(C)C>CN(C)C=O>[O:1]1[CH:5]=[N:4][N:3]=[C:2]1[CH:6]([NH:15][C:31]([C:29]1[CH:28]=[CH:27][C:25]2[NH:26][C:22]([C:19]3[CH:20]=[CH:21][N:16]=[CH:17][CH:18]=3)=[N:23][C:24]=2[CH:30]=1)=[O:32])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 697111551-[1,3,4]Oxadiazole-2-yl-3-phenylpropylamineHCID 178524160HCID 178524160, compound

Product 1

HCID 1785232812-pyridin-4-yl-1H-benzimidazole-5-carboxylic acid (1-[1,3,4]oxadiazol-2-yl-3-phenylpropyl)amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

220 mg of 1-[1,3,4]oxadiazole-2-yl-3-phenylpropylamine were dissolved in 10 ml of dry dimethylformamide at RT, treated with 260 mg of 2-pyridin-4-yl-1H-benzimidazol-5-carboxylic acid, 350 mg of TOTU, and 0.15 ml of diisopropylamine, and stirred at RT for 4 h. The reaction mixture was concentrated, the residue was taken up in ethyl acetate, and the mixture was washed successively with water, saturated sodium hydrogencarbonate solution, water, and saturated sodium chloride solution. The organic phase was dried over magnesium sulfate, filtered, and concentrated. The residue was chromatographed on silica gel using dichloromethane/methanol (8/1) and yielded 2-pyridin-4-yl-1H-benzimidazole-5-carboxylic acid (1-[1,3,4]oxadiazol-2-yl-3-phenylpropyl)amide, which melts at 103° C. with decomposition.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washthe mixture was washed successively with water, saturated sodium hydrogencarbonate solution, water, and saturated sodium chloride solution
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-3026923cd43a4aef8ee7c8a1e3428a01
Source dataset
uspto-grants-2002_03
Patent number
US06358978B1

Reaction notes

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