Diisopropylethylamine → HCID 178516784, compound

HRID 2053776Notes

Reaction equation

HRID 2053776 reaction equation
[Cl:1][C:2]1[C:3](=C=O)[CH:4]([CH:19]=[CH:20][C:21]=1O)[C:5]([NH:7][CH2:8][C:9]1[NH:13][C:12]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:11]=2[N:10]=1)=[O:6].CN([C:28]([O:32]N1N=NC2C=CC=CC1=2)=[N+:29]([CH3:31])[CH3:30])C.[B-](F)(F)(F)F.C(N(C(C)C)CC)(C)C.[O:56]=[C:57]1CNC[CH2:59][NH:58]1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[C:28]([N:29]1[CH2:30][CH2:59][NH:58][C:57](=[O:56])[CH2:31]1)=[O:32])[C:5]([NH:7][CH2:8][C:9]1[NH:13][C:12]2[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:11]=2[N:10]=1)=[O:6]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 231360Piperazin-2-oneHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178519741HCID 178519741, compound

Product 1

HCID 178516784HCID 178516784, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.182 g (0.50 mmol) of 3-chloro-N-(5-chloro-1H-benzimidazol-2-ylmethyl)-4-hydroxy-carbonylbenzamide is dissolved in 5 mL of N,N-dimethylformamide and 160.5 mg (0.50 mmol) of TBTU and 85.6 μL (0.50 mmol) of diisopropylethylamine are added successively with stirring at ambient temperature. Then a solution of 50 mg (0.50 mmol) of 2-oxopiperazine in 5 mL of N,N-dimethylformamide is added dropwise and the reaction mixture is stirred for 3 hours at ambient temperature. Then the solvent is eliminated in vacuo and the residue purified by chromatography on silica gel (gradient: dichloromethane/methanol=100:0 □93:7). Yield: 99 mg (44%); C20H17C12N5O3 (446.30); mass spectrum: (M+H)+=446/448/450 (chlorine isotope).

Workup

  1. stirringthe reaction mixture is stirred for 3 hours at ambient temperature
  2. customthe residue purified by chromatography on silica gel (gradient: dichloromethane/methanol=100:0 □93:7)

Sources & evidence

ORD record
ord-28be2ab9c4a446d08b570352d0b709a7
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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