Potassium Carbonate → 4-{5-[3-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-ureido]-pyridin-2-ylamino}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1993696Notes

Reaction equation

HRID 1993696 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:17][C:18](=O)[O:19]CC(Cl)(Cl)Cl)[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:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([NH:39][C:40]2[CH:45]=[CH:44][C:43]([NH2:46])=[CH:42][N:41]=2)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:26]([O:30][C:31]([N:33]1[CH2:34][CH2:35][CH:36]([NH:39][C:40]2[CH:45]=[CH:44][C:43]([NH:46][C:18]([NH:17][C:7]3[N:8]([C:10]4[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=4)[N:9]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=3)=[O:19])=[CH:42][N:41]=2)[CH2:37][CH2:38]1)=[O:32])([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 99310942,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamateHCID 53255724tert-Butyl 4-(5-aminopyridin-2-ylamino)piperidine-1-carboxylate

Product 1

HCID 685418894-{5-[3-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-ureido]-pyridin-2-ylamino}-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Add (5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-carbamic acid, 2,2,2-trichloro-ethyl ester (Preparation 38, 2.0 mmol, 0.8 g) over a solution of 4-(5-amino-pyridin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (2.0 mmol, 0.6 g) and potassium carbonate (2.20 mmol, 0.3 g) in acetonitrile (25 mL). Stir the solution for 12 hours at room temperature. Add water and extract with CH2Cl2. Combine the organic layers and wash with saturated aq. sodium chloride, dry over sodium sulfate, filter, and concentrate under reduced pressure to give a residue. Subject residue to silica gel chromatography eluting with CH2Cl2: MeOH in gradient (from 0.5 to 20%) to yield 4-{5-[3-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-ureido]-pyridin-2-ylamino}-piperidine-1-carboxylic acid tert-butyl ester. MS(ES+): m/z=548 [M+H])

Workup

  1. extractionAdd water and extract with CH2Cl2
  2. washwash with saturated aq. sodium chloride
  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 CH2Cl2

Sources & evidence

ORD record
ord-3e706d0af790423a936d8e6edfbc6f69
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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