Triethylamine → 1-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-{5-chloro-6-[4-(1-methyl-cyclopropanecarbonyl)-piperazin-1-yl]-pyridin-3-yl}-urea

HRID 1993707Notes

Reaction equation

HRID 1993707 reaction equation
Cl.[C:2]([C:6]1[CH:7]=[C:8]([NH:18][C:19]([NH:21][C:22]2[CH:23]=[N:24][C:25]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[C:26]([Cl:28])[CH:27]=2)=[O:20])[N:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[N:10]=1)([CH3:5])([CH3:4])[CH3:3].[CH3:35][C:36]1([C:39](O)=[O:40])[CH2:38][CH2:37]1.O.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C>C(Cl)Cl>[C:2]([C:6]1[CH:7]=[C:8]([NH:18][C:19]([NH:21][C:22]2[CH:23]=[N:24][C:25]([N:29]3[CH2:34][CH2:33][N:32]([C:39]([C:36]4([CH3:35])[CH2:38][CH2:37]4)=[O:40])[CH2:31][CH2:30]3)=[C:26]([Cl:28])[CH:27]=2)=[O:20])[N:9]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[N:10]=1)([CH3:5])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 813261-Methylcyclopropanecarboxylic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 685368151-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-(5-chloro-6-piperazin-1-yl-pyridin-3-yl)-urea hydrochloride

Product 1

HCID 685418541-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-{5-chloro-6-[4-(1-methyl-cyclopropanecarbonyl)-piperazin-1-yl]-pyridin-3-yl}-urea

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Over a solution of 1-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-(5-chloro-6-piperazin-1-yl-pyridin-3-yl)-urea hydrochloride (1.6 mmol, 0.7 g), in 5 mL of CH2Cl2 add 1-methyl-cyclopropanecarboxylic acid (1.6 mmol, 0.2 g), 1-hydroxy-1H-benzotriazol hydrate (1.8 mmol, 0.2 g), N-ethyl-N′-(3-domethylaminopropyl) carbodiimide hydrochloride (1.8 mmol, 0.3 g) and triethylamine (4.8 mmol, 0.7 mL). Stir the solution for 24 hours at room temperature. Add water and extract with CH2Cl2. Combine the organic layers and wash with saturated aq. sodium chloride solution, dry over sodium sulfate, filter, and concentrate under reduced pressure to give a residue. Subject residue to silica gel chromatography eluting with hexanes/ethyl acetate in gradient (from 20% to 80%). MS(ES+): m/z=550 [M+H].

Workup

  1. extractionAdd water and extract with CH2Cl2
  2. washwash with saturated aq. sodium chloride solution
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customto give a residue
  7. washSubject residue to silica gel chromatography eluting with hexanes/ethyl acetate in gradient (from 20% to 80%)

Sources & evidence

ORD record
ord-581ace9d217f4cbf916b2d3654fcbf96
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

Loading…