Benzyl isocyanate → Methyl 3-[5-(3-{[benzylamino]carbonylamino}propoxy)indolyl]propanoate

HRID 23987Notes

Reaction equation

HRID 23987 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:9]2.[CH2:21]([N:28]=[C:29]=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(#N)C>[CH2:21]([NH:28][C:29]([NH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]([CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:9]2)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 66819503Methyl 3-[5-(aminopropoxy)indolyl]propanoate

Product 1

HCID 22570288Methyl 3-[5-(3-{[benzylamino]carbonylamino}propoxy)indolyl]propanoateYield 42%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To the solution of methyl 3-[5-(aminopropoxy)indolyl]propanoate (140 mg, 0.5 mmol), as prepared in the preceding step, in acetonitrile (10 mL) was added benzyl isocynate (135 mg, 1.0 mmol), and the mixture was stirred at ambient temperature overnight. After evaporating the solvent in vacuo, the residue was purified by flash column chromatography on silica gel (methylene chloride to 5% ethyl acetate in methylene chloride) to give the title compound as a white solid (85 mg, 42%). 1H-NMR (400 MHz, CDCl3) δ 7.28 (m, 5H), 7.20 (d, J=8.9 Hz, 1H), 7.10 (d, J=2.8 Hz, 1H), 7.05 (d, J=2.5 Hz, 1H), 6.81 (dd, J=8.8, 2.5 Hz, 1H), 6.38 (d, J=2.9 Hz, 1H), 4.66 (br s, 2H), 4.41 (t, J=6.8 Hz, 2H), 4.35 (d, J=5.7 Hz, 2H), 4.06 (t, J=5.8 Hz, 2H), 3.66 (s, 3H), 3.43 (q, J=6.2 Hz, 2H), 2.81 (t, J=6.8 Hz, 2H), 1.99 (t, J=6.1, 2H).

Workup

  1. customAfter evaporating the solvent in vacuo
  2. customthe residue was purified by flash column chromatography on silica gel (methylene chloride to 5% ethyl acetate in methylene chloride)

Sources & evidence

ORD record
ord-14aec1e9b3f74212a43cb4f44187fb0e
Source dataset
uspto-grants-2005_02
Patent number
US06855722B2

Reaction notes

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