Dimethylformamide → HCID 67550203, compound

HRID 1071798Notes

Reaction equation

HRID 1071798 reaction equation
O[C:2]([C:4]1N(C)[CH:7]=[C:6]([NH:10][C:11]([C:13]2[NH:14][C:15]3[C:20]([CH:21]=2)=[CH:19][C:18]([C:22](NC2C=C(C(O)=O)N(C)C=2)=[O:23])=[CH:17][CH:16]=3)=[O:12])[CH:5]=1)=O.[CH2:34]([O:36][C:37]([C:39]1[NH:40][C:41]2[C:46]([CH:47]=1)=[CH:45][C:44]([NH2:48])=[CH:43][CH:42]=2)=[O:38])[CH3:35].N[C:50]1[CH:51]=[C:52]([C:56]([O:58][CH3:59])=[O:57])[N:53](C)C=1.[CH3:60]N(C=O)C>>[CH2:34]([O:36][C:37]([C:39]1[NH:40][C:41]2[C:46]([CH:47]=1)=[CH:45][C:44]([NH:48][C:22]([C:18]1[CH:19]=[C:20]3[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:11](=[O:12])[NH:10][C:6]1[CH:7]=[C:50]4[C:2](=[CH:4][CH:5]=1)[NH:53][C:52]([C:56]([O:58][CH2:59][CH3:60])=[O:57])=[CH:51]4)=[CH:21]3)=[O:23])=[CH:43][CH:42]=2)=[O:38])[CH3:35]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 2794657HCID 2794657, compoundHCID 10726872Ethyl 5-amino-1H-indole-2-carboxylateHCID 67550255HCID 67550255, compound

Product 1

HCID 67550203HCID 67550203, compoundYield 66%

Procedure

A solution of compound 2 (200 mg, 0.372 mmole) and freshly prepared of 5-aminoindole-2-carboxylic acid ethyl ester (as described above) methyl 4-amino-1-methyl-1H-pyrrole-2-carboxylate in dry DMF (5.0 ml) was kept at ambient temperature for 48 hours and evaporated. The residue was re-precipitated from DMF (1.0 ml)-0.01 M HCl (10 ml). The precipitate was collected on the filter, washed with water (3×5 ml) end ether (2×3 ml) and dried in vacuo over phosphorus pentoxide to give 142 mg (66%) of 5-({1-[2-(2-ethoxycarbonyl-1H-indol-5-ylcarbamoyl)-1H-indol-5-yl]-methanoyl}-amino)-1H-indole-2-carboxylic acid ethyl ester 21. The structure was confirmed by ES MS and 1H-NMR.

Workup

  1. customevaporated
  2. customThe residue was re-precipitated from DMF (1.0 ml)-0.01 M HCl (10 ml)
  3. customThe precipitate was collected on the filter
  4. washwashed with water (3×5 ml) end ether (2×3 ml)
  5. dry with materialdried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-11cadc3b8d9744d4a029a8c99b565bce
Source dataset
uspto-grants-2005_06
Patent number
US06906103B2

Reaction notes

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