Aniline → HCID 58653679, compound

HRID 1676092Notes

Reaction equation

HRID 1676092 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]([OH:24])=O)=[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(O[N:43]1N=N[C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][C:44]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.NC1C=CC=CC=1>CN(C=O)C>[NH:43]([C:22]([C:20]1[CH:19]=[CH:18][C:17]2[N:13]([CH:6]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:25])[CH:14]=[N:15][C:16]=2[CH:21]=1)=[O:24])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 58653638HCID 58653638, compound

Product 1

HCID 58653679HCID 58653679, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(3-ethoxy-3-oxo-1-phenylpropyl)-1H-benzimidazole-5-carboxylic acid (50 mg, 148 μmol) in DMF (3 μL) was added N,N-diisopropylethylamine (50 μL, 287 μmol) and TBTU (57 mg, 177 μmol). The solution was stirred at room temperature for 0.5 hour, aniline (20 μL, 220 μmol) was added, and stirring continued at room temperature for 72 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 (98:2) to afford the title compound, [LCMS (Method A, Mobile Phase I) RT=5.30 min, MH+ 414].

Workup

  1. stirringstirring
  2. waitcontinued at room temperature for 72 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 (98:2)

Sources & evidence

ORD record
ord-6601e1b0fbe145bb8095a660453ff46d
Source dataset
uspto-grants-2011_08
Patent number
US08003806B2

Reaction notes

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