Potassium Carbonate → HCID 59637265, compound

HRID 2194942Notes

Reaction equation

HRID 2194942 reaction equation
[C:1]([C:5]1[CH:9]=[C:8]([CH2:10][NH2:11])[N:7]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl[C:26]([O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:27].C(OCC)(=O)C.CCCCCC>CN(C=O)C>[C:29]1([O:28][C:26](=[O:27])[NH:11][CH2:10][C:8]2[N:7]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([Cl:18])[CH:13]=3)[N:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH:9]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 21226206Ethyl acetate hexaneHCID 58093530(3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methanamine

Product 1

HCID 59637265HCID 59637265, compoundYield 46.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (3-tert-butyl-1-(3-chlorophenyl)-1H-pyrazol-5-yl)methanamine (5 g, 0.018 mol) in DMF (25 ml, 5 times), potassium carbonate (9.16 g, 0.066 mol, 3.5 eq) was added and cooled the contents to 0° C. Then phenyl chloroformate (3.28 g (2.65 ml), 0.02 mol, 1.1 eq) was added drop wise for 15 min and the overall reaction mixture was stirred for another 15 min at 0° C. Progress of the reaction was monitored by TLC (20% ethyl acetate/hexane, Rf˜0.3). On completion of the reaction, reaction contents were filtered, filtrate was diluted with cold water (100 ml) and the product extracted with ethyl acetate (3×25 ml). Combined organic layer was washed with brine solution (100 ml), dried over sodium sulfate and concentrated under reduced pressure. Crude obtained was purified by column chromatography (silica gel, 10% ethyl acetate/hexane) to yield the required product as a white solid (3.2 g, 45% yield).

Workup

  1. customOn completion of the reaction, reaction contents
  2. filtrationwere filtered
  3. additionfiltrate was diluted with cold water (100 ml)
  4. extractionthe product extracted with ethyl acetate (3×25 ml)
  5. washCombined organic layer was washed with brine solution (100 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customCrude obtained
  9. customwas purified by column chromatography (silica gel, 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-ecd2d30141a942efa5b14f8403deba12
Source dataset
uspto-grants-2012_12
Patent number
US08334315B2

Reaction notes

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