Diisopropylethylamine → HCID 58653629, compound

HRID 1676094Notes

Reaction equation

HRID 1676094 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][CH:6]([N:13]1[C:17]2[CH:18]=[CH:19][C:20]([C:22](O)=[O:23])=[CH:21][C:16]=2[N:15]=[CH:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].C(N(CC)C(C)C)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[N:57]1[CH:62]=[CH:61][N:60]=[CH:59][C:58]=1[N:63]1[CH2:68][CH2:67][NH:66][CH2:65][CH2:64]1>CN(C=O)C>[C:7]1([CH:6]([N:13]2[C:17]3[CH:18]=[CH:19][C:20]([C:22]([N:66]4[CH2:65][CH2:64][N:63]([C:58]5[CH:59]=[N:60][CH:61]=[CH:62][N:57]=5)[CH2:68][CH2:67]4)=[O:23])=[CH:21][C:16]=3[N:15]=[CH:14]2)[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:25])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27346391-PiperazinylpyrazineHCID 58653638HCID 58653638, compound

Product 1

HCID 58653629HCID 58653629, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(3-ethoxy-3-oxo-1-phenylpropyl)-1H-benzimidazole-5-carboxylic acid (70 mg, 207 μmol) in DMF (4 mL) was added N,N-diisopropylethylamine (40 μL, 229 μmol) and TBTU (80 mg, 249 μmol). The solution was stirred at room temperature for 0.5 hour, 1-(2-pyrazinyl) piperazine (41 mg, 249 μmol) was added, and stirring continued at room temperature for 24 hours. The solution was evaporated in vacuo, and the residue was purified by flash column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (95:5) to afford the title compound, [LCMS (Method A, Mobile Phase I) RT=4.33 min, MH+ 485].

Workup

  1. stirringstirring
  2. waitcontinued at room temperature for 24 hours
  3. customThe solution was evaporated in vacuo
  4. customthe residue was purified by flash column chromatography on silica gel
  5. washeluting with a mixture of dichloromethane and methanol (95:5)

Sources & evidence

ORD record
ord-7c89791204264434a60e61de16628bf3
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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