Triethylamine → 5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl-3-{6-[4-(2,2-dimethyl-propionyl)-piperazin-1-yl]-pyridin-3-yl}-urea

HRID 1993702Notes

Reaction equation

HRID 1993702 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:17][C:18]([NH:20][C:21]2[CH:22]=[N:23][C:24]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[CH:25][CH:26]=2)=[O:19])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:40][C:41]([CH3:46])([CH3:45])[C:42](Cl)=[O:43]>C(Cl)Cl>[C:1]([C:5]1[CH:6]=[C:7]([NH:17][C:18]([NH:20][C:21]2[CH:22]=[N:23][C:24]([N:27]3[CH2:28][CH2:29][N:30]([C:42](=[O:43])[C:41]([CH3:46])([CH3:45])[CH3:40])[CH2:31][CH2:32]3)=[CH:25][CH:26]=2)=[O:19])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 685379841-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-(6-piperazin-1-yl-pyridin-3-yl)-urea

Product 1

HCID 686250775-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl-3-{6-[4-(2,2-dimethyl-propionyl)-piperazin-1-yl]-pyridin-3-yl}-ureaYield 73.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Place 1-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-(6-piperazin-1-yl-pyridin-3-yl)-urea (200 mg, 0.461 mmol), triethylamine (0.071 mL, 0.507 mmol), and 4-N,N-dimethylaminopyridine (6 mg, 0.051 mmol) in CH2Cl2 (10 mL). Add 2,2-dimethyl-propionyl chloride (0.062 mL, 0.507 mmol) and stir at room temperature for 17 h. Subject residue to silica gel chromatography eluting with 0-100% EtOAc:hexane to yield 175 mg (73%) of the title compound. MS(ES+): m/z=518.2 [M+H].

Workup

  1. washSubject residue to silica gel chromatography eluting with 0-100% EtOAc

Sources & evidence

ORD record
ord-58d1404b5dd84e9f986b718d01373afc
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

Loading…