Triethylamine → 5-(1H-Indol-3-ylmethyl)-3-(2-morphlin-4-yl-ethyl)-2-thioxo-imidazolidin-4-one

HRID 401605Notes

Reaction equation

HRID 401605 reaction equation
Cl.CO[C:4](=[O:17])[C@H:5]([CH2:7][C:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][CH:9]=1)[NH2:6].C(N(CC)CC)C.[N:25]([CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1)=[C:26]=[S:27]>ClCCl>[NH:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:8]([CH2:7][CH:5]2[NH:6][C:26](=[S:27])[N:25]([CH2:28][CH2:29][N:30]3[CH2:31][CH2:32][O:33][CH2:34][CH2:35]3)[C:4]2=[O:17])=[CH:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1439572-Morpholinoethyl isothiocyanateHCID 2734891Methyl tryptophanate hydrochloride

Product 1

HCID 573776065-(1H-Indol-3-ylmethyl)-3-(2-morphlin-4-yl-ethyl)-2-thioxo-imidazolidin-4-oneYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of L-tryptophan methyl ester hydrochloride (0.250 mg, 0.001 mol.) in dichloromethane (10 mL) was added triethyl amine (3.0 eq.) followed by 4-(2-isothiocyanato-ethyl)-morpholine (0.190 gm, 0.0011 mol.). The reaction mixture was stirred at room temperature for 24 hr, and then concentrated. The residue obtained was purified by column chromatography on silica gel using 60% ethyl acetate-hexane to give 893-17 (292 mg, 83%): mp 167-169° C., 1H NMR (500 MHz, CDCl3): 2.45-2.51 (m, 6H), 3.02-3.07 (dd, J=9.5 and 15.0 Hz, 1H), 3.46-3.50 (dd, J=4.0 and 15.0 Hz, 1H), 3.65 (m, 4H) 3.89 (d, J=7.0 Hz, 2H), 4.35-4.38 (m, 1H), 6.38 (s, 1H), 7.12 (d, J=2.5 Hz, 1H), 7.16-7.19 (m, 1H), 7.23-7.25 (dd, J=1.5 and 8.0 Hz, 1H), 7.39 (d, J=8.5 Hz, 1H), 7.61 (d, J=8.5 Hz, 1H), 8.15 (s, 1H).

Workup

  1. concentrationconcentrated
  2. customThe residue obtained
  3. customwas purified by column chromatography on silica gel using 60% ethyl acetate-hexane

Sources & evidence

ORD record
ord-13fa49f01c5a469cbd3c36e004716715
Source dataset
uspto-grants-2014_06
Patent number
US08741942B2

Reaction notes

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