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

HRID 1993703Notes

Reaction equation

HRID 1993703 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].[CH3:33][CH:34]([CH2:39][CH3:40])[CH2:35][C:36](O)=[O:37].O.ON1C2C=CC=CC=2N=N1.N=C=N>C(Cl)Cl.CN(C=O)C>[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:36](=[O:37])[CH2:35][CH:34]([CH3:33])[CH2:39][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

6

Reactant 4

HCID 77553-Methylpentanoic acidHCID 160435CarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 685379841-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-(6-piperazin-1-yl-pyridin-3-yl)-urea

Product 1

HCID 685400261-(5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-{6-[4-(3-methyl-pentanoyl)-piperazin-1-yl]-pyridin-3-yl}-ureaYield 55.2%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

React 1-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-(6-piperazin-1-yl-pyridin-3-yl)-urea (0.20 g, 0.46 mmol) with 3-methyl-pentanoic acid (0.059 g, 0.51 mmol), 1-hydroxybenzotriazole hydrate (0.06 g, 0.46 mmol) and polymer supported carbodiimide (0.83 g, 1.0 mmol), suspended in a mixture CH2Cl2/DMF (18/1, mL). Stir the mixture at room temperature overnight and then filter and wash the resin with CH2Cl2. Concentrate and purify the residue with a SCX cartridge eluting with NH4OH/CH3OH 2N to yield 135 mg (55%) of the title compound as a pale pink solid. MS(ES+): m/z=532 [M+H].

Workup

  1. filtrationfilter
  2. washwash the resin with CH2Cl2
  3. concentrationConcentrate
  4. custompurify the residue with a SCX cartridge
  5. washeluting with NH4OH/CH3OH 2N

Sources & evidence

ORD record
ord-fb2fcb80b3d84d43a337eed10122a9a6
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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