Ethylenediamine → 4-[N'-(2-aminoethyl)thioureido]-1-t-butoxycarbonyl-2,3-dihydro-7-methylindole

HRID 1275671Notes

Reaction equation

HRID 1275671 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([N:18]=[C:19]=[S:20])[CH:13]=[CH:14][C:15]=2[CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([NH2:24])[CH2:22][NH2:23]>C(Cl)Cl>[NH2:23][CH2:22][CH2:21][NH:24][C:19](=[S:20])[NH:18][C:12]1[CH:13]=[CH:14][C:15]([CH3:17])=[C:16]2[C:11]=1[CH2:10][CH2:9][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 224612381-t-Butoxycarbonyl-2,3-dihydro-4-isothiocyanato-7-methylindole

Product 1

HCID 542320044-[N'-(2-aminoethyl)thioureido]-1-t-butoxycarbonyl-2,3-dihydro-7-methylindoleYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-t-butoxycarbonyl-2,3-dihydro-4-isothiocyanato-7-methylindole (1.70 g; 5.86 mmol) in methylene chloride (10 mL) is slowly added to a solution of ethylenediamine (1.76 g, 29.3 mmol) in methylene chloride (10 mL). After 30 minutes, the solution is washed with four 50-mL portions of aqueous potassium carbonate, dried over anhydrous potassium carbonate, filtered and rotary evaporated to yield an off-white solid. The crude residue is purified via silica gel column chromatography using 10% methanol (ammonium hydroxide treated)/methylene chloride as the eluent. The appropriate fractions are combined and the solvents removed by rotary evaporation to yield 1.92 g of 4-[N'-(2-aminoethyl)thioureido]-1-t-butoxycarbonyl-2,3-dihydro-7-methylindole as a white solid (94% yield).

Workup

  1. washthe solution is washed with four 50-mL portions of aqueous potassium carbonate
  2. dry with materialdried over anhydrous potassium carbonate
  3. filtrationfiltered
  4. customrotary evaporated
  5. customto yield an off-white solid
  6. customThe crude residue is purified via silica gel column chromatography
  7. customthe solvents removed by rotary evaporation

Sources & evidence

ORD record
ord-2468eabf747b485cafdf4ff93f78887a
Source dataset
uspto-grants-2000_12
Patent number
US06162818

Reaction notes

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