Ethyl-(2-{[1-(5-nitro-1H-indol-2-yl)-methanoyl]-amino}-ethyl)-carbamic acid dimethyl-ethyl ester → 1H-indole-2,5-dicarboxylic acid bis-{[2-(2-ethylamino-ethylcarbamoyl)-1H-indol-5-yl]-amide}

HRID 1071806Notes

Reaction equation

HRID 1071806 reaction equation
CC(OC(=O)[N:7]([CH2:25][CH3:26])[CH2:8][CH2:9][NH:10][C:11]([C:13]1[NH:14]C2C([CH:21]=1)=CC([N+]([O-])=O)=CC=2)=[O:12])(C)C.F[C:29]1[C:34]([NH:35][C:36]([C:38]2[NH:39][C:40]3[C:45]([CH:46]=2)=[CH:44][C:43]([C:47]([NH:49][C:50]2[C:55](F)=[C:54](F)[C:53](F)=[C:52](F)[C:51]=2F)=[O:48])=[CH:42][CH:41]=3)=[O:37])=[C:33](F)[C:32](F)=[C:31](F)[C:30]=1F>CN(C=O)C>[CH2:25]([NH:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[NH:14][C:31]2[C:32]([CH:21]=1)=[CH:33][C:34]([NH:35][C:36]([C:38]1[NH:39][C:40]3[C:45]([CH:46]=1)=[CH:44][C:43]([C:47]([NH:49][C:50]1[CH:55]=[C:54]4[C:53](=[CH:52][CH:51]=1)[NH:14][C:13]([C:11](=[O:12])[NH:10][CH2:9][CH2:8][NH:7][CH2:25][CH3:26])=[CH:21]4)=[O:48])=[CH:42][CH:41]=3)=[O:37])=[CH:29][CH:30]=2)=[O:12])[CH3:26]

Participants

4

Reactant 2

HCID 67550180Ethyl-(2-{[1-(5-nitro-1H-indol-2-yl)-methanoyl]-amino}-ethyl)-carbamic acid dimethyl-ethyl esterHCID 858013151H-Indole-2,5-dicarboxylic acid bis-(pentafluorophenyl-amide)

Product 1

HCID 675501771H-indole-2,5-dicarboxylic acid bis-{[2-(2-ethylamino-ethylcarbamoyl)-1H-indol-5-yl]-amide}Yield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

Compound 78 (127 mg, 0.336 mmol) was reduced to 79 by hydrogenation according to general procedure A in example 10. A mixture of above amine DS13a and 1H-indole-2,5-dicarboxylic acid bis-(pentafluorophenyl-amide) 74 (45 mg, 0.084 mmol) in 2 ml of anhydrous DMF under argon was stirred at 55° C. overnight. The solvent was evaporated to dryness. The residue was dissolved in 5 ml of TFA/anisole (8:2) and the mixture was kept at room temperature for 1 h. The product was precipitated by ether and purified by HPLC described in general procedure B in example 10 to give 76 (22 mg, 40%). ESI MS: 662.27 (M+H+), 331.64 (M/2+H+).

Workup

  1. customThe solvent was evaporated to dryness
  2. dissolutionThe residue was dissolved in 5 ml of TFA/anisole (8:2)
  3. waitthe mixture was kept at room temperature for 1 h
  4. customThe product was precipitated by ether
  5. custompurified by HPLC

Sources & evidence

ORD record
ord-c50bf8fcd37e4484936dae5e9ad2524b
Source dataset
uspto-grants-2005_06
Patent number
US06906103B2

Reaction notes

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