Pyridine → HCID 19040730, compound

HRID 1683902Notes

Reaction equation

HRID 1683902 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]([CH3:15])[CH3:14].Cl[C:17]1[N:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([NH2:21])=[O:20].N1C=CC=CC=1>BrC1C=CC=CC=1>[CH3:15][N:13]([CH3:14])[CH2:12][CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:17]3[C:18]([C:19]([NH2:21])=[O:20])=[CH:22][CH:23]=[CH:24][N:25]=3)[CH:3]=2)[NH:7][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 825882-ChloronicotinamideHCID 118202113-(2-DIMETHYLAMINO-ETHYL)-1H-INDOL-5-YLAMINE

Product 1

HCID 19040730HCID 19040730, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 7961BromobenzeneSolvent

Conditions

Temperature
156 °C

Procedure

5-Amino-3-(2-dimethylaminoethyl)indole and 2-chloronicotinamide were used. Pyridine was used as base, bromobenzene was used as solvent, and the reaction was heated at reflux (156° C.) for 18 hours. Chromatography followed by recrystallization (methanol/water) of the resulting solid in afforded the title compound (36%) as a yellow solid: mp, 127.0°-129.0° C.; 13C NMR (CD3OD) δ173.0, 157.9, 152.2, 139.0, 135.4, 132.4, 129.0, 123.9, 119.1, 113.7, 113.2, 113.0, 112.5, 111.3, 61.4, 45.4, 24.3; HRMS calculated for C18H21N5O 323.1748, found 323.1726. Anal. calcd. for C18H21N5O.H2O; C, 63.33; H, 6.79; N, 20.51. Found: C, 63.19; H, 6.50; N, 20.30.

Workup

  1. temperaturethe reaction was heated
  2. customChromatography followed by recrystallization (methanol/water) of the resulting solid

Sources & evidence

ORD record
ord-93b6541a9cd948bd8953eb69b49a3497
Source dataset
uspto-grants-1997_06
Patent number
US05639752

Reaction notes

Loading…