HCID 68408114, compound → HCID 68406752, compound

HRID 888010Notes

Reaction equation

HRID 888010 reaction equation
Cl.Cl.Cl.[NH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12](=[O:35])[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:24]=[C:23]([CH2:25][CH2:26][CH2:27][NH:28][N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[N:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1>O.[OH-].[NH4+]>[NH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12](=[O:35])[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[N:24]=[C:23]([CH2:25][CH2:26][CH2:27][NH:28][N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[N:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1

Participants

4

Reactant 1

HCID 68408114HCID 68408114, compound

Product 1

HCID 68406752HCID 68406752, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 14923Ammonium HydroxideCatalystHCID 962WaterSolvent

Procedure

N-(2-Aminophenyl)-4-[2-(3-morpholinoaminopropyl)-pyrimidin-6-yl]benzamide trihydrochloride (Method 19, 28 mg, 0.052 mmol) was dissolved in water (2 ml) and basified to pH 10 by the of addition of 28% aqueous ammonium hydroxide solution (2 drops). The resultant precipitate was collected by filtration and dried under vacuum at 40° C. overnight to afford the title compound as a yellow solid (9 mg, 40%); NMR (DMSO-d6): 1.75 (m, 2H), 2.37 (m, 6H), 3.41 (brm, 2H), 3.59 (m, 4H), 4.92 (s, 2H), 6.62 (t, 1H), 6.80 (d, 1H), 6.99 (t, 1H), 7.21 (m, 2H), 7.28 (t, 1H), 8.11 (d, 2H), 8.22 (d, 2H), 8.39 (d, 1H), 9.74 (s, 1H); Mass Spectrum: M+H+ 433.

Workup

  1. filtrationThe resultant precipitate was collected by filtration
  2. customdried under vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-f7fea66de98d438cad24144aa8a370fb
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

Loading…