Methyl 6-(aminomethyl)pyridine-3-carboxylate--hydrogen chloride (1/1) → HCID 67078580, compound

HRID 2360082Notes

Reaction equation

HRID 2360082 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:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][N:25]=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:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][N:25]=2)=[O:20])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 66667743Methyl 6-(aminomethyl)pyridine-3-carboxylate--hydrogen chloride (1/1)HCID 67078793HCID 67078793, compound

Product 1

HCID 67078580HCID 67078580, compoundYield 91%

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 6-(aminomethyl)nicotinate hydrochloride, yielding the title compound. Methyl 6-[({[3-(4-fluorophenyl)-5-(2-thienyl)-1H-pyrrol-2-yl]carbonyl}amino)methyl]nicotinate: Yield 91%; m.p. 174-176° C.; IR 3378, 3245, 1723, 1618, 1505, 1433, 1218, 1113, 843 cm−1; 1H-NMR (500 MHz, δ ppm, CDCl3) 9.45 (sb, 1H), 8.95 (s, 1H), 8.21 (dd, J=8.1 Hz, J′=2.1 Hz, 1H), 7.48 (dd, J=8.6 Hz, J′=5.4 Hz, 2H), 7.31-7.23 (m, 2H), 7.21 (d, J=3.6 Hz, 1H), 7.15 (t, J=8.6 Hz, 2H), 7.06 (dd, J=5.0 Hz, J′=3.7 Hz, 1H), 6.88 (tb, J=4.6 Hz, 1H), 6.40 (d, J=3.0 Hz, 1H), 4.65 (d, J=5.0 Hz, 2H), 3.96 (s, 3H); 13C-NMR (126 MHz, δ ppm, DMSO-d6) 165.9, 162.9, 161.0, 157.9, 150.0, 142.4, 138.7, 138.3, 136.7, 130.8, 128.6, 128.0, 127.6, 127.2, 122.6, 122.4, 119.3, 116.2, 116.0, 109.1, 51.5, 48.7.

Workup

  1. customThis material was prepared

Sources & evidence

ORD record
ord-e8a3b08c9b1249e1a76b22c1d774cf6e
Source dataset
uspto-grants-2014_04
Patent number
US08685992B2

Reaction notes

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