2-(Tritylthio)ethylamine hydrochloride → HCID 51038885, compound

HRID 2360089Notes

Reaction equation

HRID 2360089 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:11][C:10]=2[C:20]([NH:22][CH2:23][C:24]2[CH:32]=[CH:31][C:27]([C:28](O)=[O:29])=[CH:26][CH:25]=2)=[O:21])=[CH:5][CH:4]=1.Cl.C([S:53][CH2:54][CH2:55][NH2:56])(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:11][C:10]=2[C:20]([NH:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([C:28]([NH:56][CH2:55][CH2:54][SH:53])=[O:29])=[CH:31][CH:32]=2)=[O:21])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 184272672-(Tritylthio)ethylamine hydrochlorideHCID 67078571HCID 67078571, compound

Product 1

HCID 51038885HCID 51038885, compound

Procedure

This material was prepared using a method substantially similar to that of Example 22 from 4-[({[3-(4-methoxyphenyl)-5-phenyl-1H-pyrrol-2-yl]carbonyl}amino)methyl]benzoic acid and 2-(tritylsulfanyl)ethanamine hydrochloride, yielding the title compound 3-(4-methoxyphenyl)-5-phenyl-N-(4-{[(2-sulfanylethyl)amino]carbonyl}benzyl)-1H-pyrrole-2 carboxamide: Yield 70%; m.p. 131-132° C.; IR 3396, 3280, 1635, 1524, 1499, 1246 cm−1; 1H-NMR (500 MHz, δ ppm, CDCl3) 9.99 (s, 1H), 7.72 (d, J=8.1 Hz, 2H), 7.59 (d, J=7.6 Hz, 2H), 7.38 (t, J=7.7 Hz, 2H), 7.35 (d, J=8.5 Hz, 2H), 7.28 (t, J=7.5 Hz, 1H); 7.17 (d, J=8.0 Hz, 2H), 7.03 (t, J=5.5 Hz, 1H), 6.89 (d, J=8.5 Hz, 2H), 6.47 (d, J=2.9 Hz, 1H), 6.17 (t, J=5.8 Hz, 1H), 4.45 (d, J=5.9 Hz, 2H), 3.85-3.73 (m, 5H), 2.97 (t, J=6.2 Hz, 2H), 1.62 (s, 1H); 13C-NMR (75 MHz, δ ppm, CDCl3) 167.7, 161.7, 159.6, 142.4, 134.6, 133.4, 131.6, 130.8, 129.6, 129.2, 128.7, 128.5, 128.3, 127.7, 127.6, 124.9, 122.3, 114.7, 109.8, 55.6, 43.1, 39.5, 38.4, 29.9.

Workup

  1. customThis material was prepared

Sources & evidence

ORD record
ord-f1a606078202406aa487296bdec55711
Source dataset
uspto-grants-2014_04
Patent number
US08685992B2

Reaction notes

Loading…