Pyridine → 3-(3-tert-butyl-1-phenyl-1H-pyrazol-5-yl)-1-{4-[2-(morpholin-4-yl)ethoxy]naphthalen-1-yl}urea

HRID 895779Notes

Reaction equation

HRID 895779 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:10][C:11]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([O:24][CH2:25][CH2:26][N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:16][CH:15]=2)=[O:12])[NH:8][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([C:5]1[CH:6]=[C:7]([NH:10][C:11]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]([O:24][CH2:25][CH2:26][N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:16][CH:15]=2)=[O:12])[N:8]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 1049PyridineHCID 66827Phenylboronic AcidHCID 178441175HCID 178441175, compound

Product 1

HCID 98926583-(3-tert-butyl-1-phenyl-1H-pyrazol-5-yl)-1-{4-[2-(morpholin-4-yl)ethoxy]naphthalen-1-yl}ureaYield 77.9%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of the above urea (0.022 g, 0.050 mmol), phenylboronic acid (0.012 g, 0.1 mmol), copper (II) acetate (0.014 g, 0.075 mmol), pyridine (0.01 mL, 0.1 mmol) and molecular sieves (4 Å activated, 0.030 g) in methylene chloride (2 mL) was stirred at room temperature for 14 h under air. After filtration through diatomaceous earth, the filtrate was concentrated in vacuo and purified by flash chromatography (EtOAc 100% to EtOH 100%) to give the title compound as a yellow-white solid (0.02 g, 73%), mp 142-143° C.; 1H NMR (DMSO) δ 1.26(s, 9H), 2.53(t, 4H) 2.83(t, 2H), 3.57(t, 4H), 4.24(t, 2H), 6.34(s, 1H), 6.94(d, 1H), 7.40(d, 1H), 7.55(m, 7H), 7.90(d, 1H), 8.15(d, 1H), 8.82(s, 1H), 8.92(s, 1H); MS (CI) 514(M++H).

Workup

  1. filtrationAfter filtration through diatomaceous earth
  2. concentrationthe filtrate was concentrated in vacuo
  3. custompurified by flash chromatography (EtOAc 100% to EtOH 100%)

Sources & evidence

ORD record
ord-237e40ec79da432487ced0807d3b18de
Source dataset
uspto-grants-2005_07
Patent number
US06916924B2

Reaction notes

Loading…