Dibenzylamine → HCID 16661907, compound

HRID 533372Notes

Reaction equation

HRID 533372 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11](=[O:15])[C:12]([OH:14])=O)=[CH:3]1.[CH2:16]([NH:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CC#N>[CH2:24]([N:23]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:12](=[O:14])[C:11]([C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:2]([CH3:1])[CH:3]=1)=[O:15])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 7656DibenzylamineHCID 4589028N-Methyl-3-indoleglyoxylic acid

Product 1

HCID 16661907HCID 16661907, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N,N-Dibenzyl-2-(1-methyl-1H-indol-3-yl)-2-oxo-acetamide was synthesized following scheme II above starting from (1-methyl-1H-indol-3-yl)-oxo-acetic acid and dibenzylamine. Yield (70%). HPLC ret. time 3.70 min, 10-99% CH3CN, 5 min run; 1H NMR (400 MHz, DMSO-d6) δ 8.28 (s, 1H), 8.12 (d, J=7.7 Hz, 1H), 7.61 (d, J=8.1 Hz, 1H), 7.43-7.25 (m, 12H), 4.55 (s, 2H), 4.40 (s, 2H), 3.93 (s, 3H); ESI-MS 383.3 m/z (MH+).

Workup

  1. customYield (70%)

Sources & evidence

ORD record
ord-7f8435f5b97044c3bedb08c29b4164d7
Source dataset
uspto-grants-2014_10
Patent number
US08853254B2

Reaction notes

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