Potassium Carbonate → HCID 68538008, compound

HRID 1993706Notes

Reaction equation

HRID 1993706 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH:17][C:18](=[O:25])OCC(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].[NH2:26][C:27]1[C:28]([CH3:45])=[CH:29][C:30]([N:33]2[CH2:38][CH2:37][N:36]([C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])[CH2:35][CH2:34]2)=[N:31][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:5]1[CH:6]=[C:7]([NH:17][C:18]([NH:26][C:27]2[CH:32]=[N:31][C:30]([N:33]3[CH2:34][CH2:35][N:36]([C:39](=[O:44])[C:40]([CH3:42])([CH3:41])[CH3:43])[CH2:37][CH2:38]3)=[CH:29][C:28]=2[CH3:45])=[O:25])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:9]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 99310942,2,2-Trichloroethyl 3-tert-butyl-1-P-tolyl-1H-pyrazol-5-ylcarbamateHCID 68538057HCID 68538057, compound

Product 1

HCID 68538008HCID 68538008, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Add (5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-carbamic acid, 2,2,2-trichloro-ethyl ester (Preparation 38, 0.32 mmol, 0.1 r) over a solution of 1-[4-(5-amino-4-methyl-pyridin-2-yl)-piperazin-1-yl]-2,2-dimethyl-propan-1-one (0.3 mmol, 0.08 g) and potassium carbonate (0.3 mmol, 0.05 g) in acetonitrile (3 mL), and stir the solution for 4 hours at 80° C. 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 hexanes/ethyl acetate in gradient (from 20% to 80%). MS(ES+): m/z=532 [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 hexanes/ethyl acetate in gradient (from 20% to 80%)

Sources & evidence

ORD record
ord-f617861c03ae450a81172f668c2e32e7
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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