HCID 67078793, compound → HCID 67078796, compound

HRID 2360083Notes

Reaction equation

HRID 2360083 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[NH:10][C:9]=2[C:18]([OH:20])=O)=[CH:4][CH:3]=1.Cl.[NH2:22][CH2:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]([O:32][CH3:33])=[O:31])=[N:28][CH:29]=1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:12]=[C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[NH:10][C:9]=2[C:18]([NH:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([C:30]([O:32][CH3:33])=[O:31])=[N:28][CH:29]=2)=[O:20])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 67078793HCID 67078793, compoundHCID 67078809HCID 67078809, compound

Product 1

HCID 67078796HCID 67078796, compoundYield 66%

Procedure

This material was prepared using a method substantially similar to that of Example 5 from 3-(4-fluorophenyl)-5-(2-thienyl)-1H-pyrrole-2-carboxylic acid and methyl 5-(aminomethyl)pyridine-2-carboxylate hydrochloride, yielding the title compound. Methyl 5-[({[3-(4-fluorophenyl)-5-(2-thienyl)-1H-pyrrol-2-yl]carbonyl}amino)methyl]pyridine-2-carboxylate: Yield 66%; m.p. 174-175° C.; IR 3398, 3255, 1733, 1643, 1541, 1432, 1258, 1121 cm−1; 1H-NMR (500 MHz, δ ppm, CDCl3) 9.59 (sb, 1H), 8.56 (s, 1H), 8.07 (d, J=8.0 Hz, 1H), 7.66 (dd, J=8.0 Hz, J′=2.1 Hz, 1H), 7.41 (dd, J=5.3 Hz, J′=2.1 Hz, 2H), 7.25 (dd, J=5.1 Hz, J′=1.0 Hz, 1H), 7.22 (dd, J=3.6 Hz, J′=1.0 Hz, 1H), 7.10 (t, J=8.6 Hz, 2H), 7.05 (dd, J=5.0 Hz, J′=3.6 Hz, 1H), 6.38 (d, J=3.0 Hz, 1H), 6.01 (tb, J=5.9 Hz, 1H), 4.53 (d, J=6.1 Hz, 2H), 4.01 (s, 3H); 13C-NMR (126 MHz, δ ppm, CDCl3) 165.6, 163.8, 161.8, 161.4, 149.1, 147.3, 137.9, 136.2, 134.3, 131.4, 131.3, 131.2, 129.7, 128.1, 127.6, 125.2, 124.8, 123.5, 121.6, 116.5, 116.3, 110.4, 53.1, 40.8.

Workup

  1. customThis material was prepared

Sources & evidence

ORD record
ord-645716c9f7014f3c826d716203f1a5b7
Source dataset
uspto-grants-2014_04
Patent number
US08685992B2

Reaction notes

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