Potassium Carbonate → HCID 57848813, compound

HRID 736263Notes

Reaction equation

HRID 736263 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:16]=[CH:15][C:11]([C:12](Cl)=[O:13])=[CH:10][CH:9]=1.[NH2:17][C:18]1[C:19]2[CH:32]=[C:31]([C:33]([NH:35][N:36]([CH3:43])[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:34])[S:30][C:20]=2[N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[N:22]=1>O1CCCC1>[Br:7][C:8]1[CH:16]=[CH:15][C:11]([C:12]([NH:17][C:18]2[C:19]3[CH:32]=[C:31]([C:33]([NH:35][N:36]([CH3:43])[C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[O:34])[S:30][C:20]=3[N:21]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[N:22]=2)=[O:13])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 685154-Bromobenzoyl chlorideHCID 57848800HCID 57848800, compound

Product 1

HCID 57848813HCID 57848813, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

169 mg (1.22 mmol) of potassium carbonate, followed by 191 mg (0.87 mmol) of 4-bromobenzoyl chloride, are added to a solution of 0.27 g (0.70 mmol) of tert-butyl 3-amino-5-(N′-methyl-N′-phenylhydrazinocarbonyl)thieno[2,3-c]pyrazole-1-carboxylate in 20 mL of tetrahydrofuran under argon. The reaction mixture is stirred at reflux for 2 hours. The reaction mixture is then cooled to a temperature in the region of 25° C. and treated with 40 mL of ice-cold water. The mixture is extracted successively with 60 mL and then with twice 40 mL of ethyl acetate. The organic phases are combined, washed twice with 40 mL of saturated brine, dried over magnesium sulfate, filtered and then concentrated to dryness under vacuum (2 kPa) at a temperature in the region of 35° C. The residue is purified by chromatography on a cartridge of 25 g of silica gel (0.015-0.040 mm), eluting successively with dichloromethane/methanol mixtures (99/1 by volume, and then 98/2) at a flow rate of 13 mL/min. The fractions containing the expected product are combined and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 35° C. 0.04 g of tert-butyl 3-(4-bromobenzoylamino)-5-(N′-methyl-N′-phenylhydrazinocarbonyl)thieno[2,3-c]pyrazole-1-carboxylate is thus obtained in the form of a white solid melting at 192° C.

Workup

  1. temperatureat reflux for 2 hours
  2. extractionThe mixture is extracted successively with 60 mL
  3. washwashed twice with 40 mL of saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under vacuum (2 kPa) at a temperature in the region of 35° C
  7. customThe residue is purified by chromatography on a cartridge of 25 g of silica gel (0.015-0.040 mm)
  8. washeluting successively with dichloromethane/methanol mixtures (99/1 by volume
  9. additionThe fractions containing the expected product
  10. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 35° C

Sources & evidence

ORD record
ord-cc491ec5e75b4e9daf9b3f8bd8829f1b
Source dataset
uspto-grants-2009_09
Patent number
US07595320B2

Reaction notes

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