Diisopropylethylamine → HCID 24815415, compound

HRID 2243169Notes

Reaction equation

HRID 2243169 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([OH:13])=O)[CH:10]=1)[NH:7][CH:6]=[CH:5]2.[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH:16]=[C:15]1[CH2:23][NH:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C.C(OCC)(=O)C>[O:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH:16]=[C:15]1[CH2:23][N:24]([CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[C:29]([Cl:34])[CH:28]=1)[C:11]([C:9]1[CH:10]=[C:2]([Cl:1])[CH:3]=[C:4]2[C:8]=1[NH:7][CH:6]=[CH:5]2)=[O:13]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 668685635-chloro-1H-indole-7-carboxylic acidHCID 67017771HCID 67017771, compound

Product 1

HCID 24815415HCID 24815415, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 72 mg (0.37 mmol) of 5-chloro-1H-indole-7-carboxylic acid and 118 mg (0.37 mmol) of benzofuran-2-ylmethyl-[2-(3,4-dichloro-phenyl)-ethyl]-amine in DMF (5 ml) were added 131 mg (0.41 mmol) of TBTU and 126 μl (0.74 mmol) of N,N-diisopropylethyl amine and the mixture was stirred over night at RT. Then the reaction mixture was diluted with ethyl acetate and washed with water, brine, sat. NaHCO3 solution, 1N HCl and again with brine. The organic layer was then dried (MgSO4) and concentrated. The remaining residue was purified by column chromatography (silica gel; ethyl acetate/cyclohexane 9:1) to yield the title compound as a yellow oil (145 mg, 79%). MS (ISP) 497.3 (M+H)+.

Workup

  1. washwashed with water, brine, sat. NaHCO3 solution, 1N HCl and again with brine
  2. dry with materialThe organic layer was then dried (MgSO4)
  3. concentrationconcentrated
  4. customThe remaining residue was purified by column chromatography (silica gel; ethyl acetate/cyclohexane 9:1)

Sources & evidence

ORD record
ord-3c3f5500b11d40118f6d3e1c13ee681c
Source dataset
uspto-grants-2010_03
Patent number
US07674815B2

Reaction notes

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