Water → HCID 18476244, compound

HRID 2187642Notes

Reaction equation

HRID 2187642 reaction equation
C[Al](C)C.[NH2:5][CH2:6][CH2:7][NH2:8].C(O[C:12](=O)[CH2:13][CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])[CH:16]=1)C.O>C1(C)C=CC=CC=1>[Cl:32][C:26]1[CH:27]=[C:28]([Cl:31])[CH:29]=[CH:30][C:25]=1[CH2:24][N:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([CH2:14][CH2:13][C:12]2[NH:5][CH2:6][CH2:7][N:8]=2)=[CH:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 3301EthylenediamineHCID 16682925TrimethylaluminumHCID 54389335HCID 54389335, compound

Product 1

HCID 18476244HCID 18476244, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Conditions

Temperature
0 °C

Procedure

A 2M solution of trimethyl aluminium in toluene (3.32 ml) was diluted with dry toluene (30 ml), cooled to 0° C. and 1,2-diaminoethane (0.43 ml) was added. The mixture was brought to ambient temperature and a solution of 2.5 g of 3-[1-(2,4-Dichlorobenzyl)-1H-indol-3-yl]-propionic acid ethyl ester in dry toluene (20 ml) was added slowly. The reaction mixture was refluxed for 15 hours, cooled and carefully hydrolysed with water (20 ml). The organic phase was separated, dried over sodium sulphate and evaporated. The crude product was purified by column chromatography using successively methylene chloride/ethanol/aqueous ammonium hydroxide 50:49:1 and 50:43:7 respectively to yield the titled product.

Workup

  1. customwas brought to ambient temperature
  2. temperatureThe reaction mixture was refluxed for 15 hours
  3. customThe organic phase was separated
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-ff336210606343d7940330e794a3eca9
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Reaction notes

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