HCID 57987110, compound → HCID 51039085, compound

HRID 2360090Notes

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](O)=[O:21])=[CH:5][CH:4]=1.Cl.[NH2:24][CH2:25][C:26]1[CH:40]=[CH:39][C:29]([C:30]([NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=[O:31])=[CH:28][CH:27]=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:24][CH2:25][C:26]2[CH:27]=[CH:28][C:29]([C:30]([NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=3)=[O:31])=[CH:39][CH:40]=2)=[O:21])=[CH:5][CH:4]=1

Participants

Reactant 2

HCID 57987110HCID 57987110, compound

HCID 67079027HCID 67079027, compound

Product 1

HCID 51039085HCID 51039085, compoundYield 71%

Procedure

This material was prepared using a method substantially similar to that of Example 5 from 3-(4-methoxyphenyl)-5-phenyl-1H-pyrrole-2-carboxylic acid and 4-(aminomethyl)-N-pyridin-2-ylbenzamide hydrochloride, yielding the title compound. 3-(4-Methoxyphenyl)-5-phenyl-N-{4-[(pyridin-2-ylamino)carbonyl]benzyl}-1H-pyrrole-2-carboxamide: Yield 71%; m.p. 196° C. (dec.); IR 3402, 3239, 1623, 1536, 1432, 1304, 1246 cm−1; 1H-NMR (300 MHz, δ ppm, CDCl3) 9.75 (s, 1H), 8.77 (s, 1H), 8.39 (d, J=8.4 Hz, 1H), 8.29 (d, J=4.8 Hz, 1H), 7.88 (d, J=8.3 Hz, 2H), 7.77 (dt, J=7.0 Hz, J′=1.8 Hz, 1H), 7.57 (d, J=7.2 Hz, 2H), 7.45-7.27 (m, 7H), 7.07 (ddd, J=7.3 Hz, J′=5.0 Hz, J″=0.8 Hz, 1H), 6.90 (d, J=8.7 Hz, 2H), 6.49 (d, J=3.0 Hz, 1H), 6.13 (t, J=5.8 Hz, 1H), 4.52 (d, J=5.9 Hz, 2H), 3.82 (s, 3H); 13C-NMR (75 MHz, δ ppm, CDCl3) 165.7, 161.6, 159.7, 151.9, 148.1, 143.0, 138.8, 134.7, 133.6, 131.6, 430.9, 129.2, 128.3, 127.9, 127.8, 127.7, 125.0, 122.4, 120.1, 114.7, 109.9, 55.6, 43.1.

Workup

customThis material was prepared

Sources & evidence

ORD record: ord-5b53d3cb784c4a41915300b1f5f9a035
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685992B2

Reaction notes

Loading…