Potassium Carbonate → HCID 178486249, compound

HRID 736259Notes

Reaction equation

HRID 736259 reaction equation
C(=O)([O-])[O-].[K+].[K+].Cl.[N:8]1([CH2:14][C:15]2[CH:23]=[CH:22][C:18]([C:19](Cl)=[O:20])=[CH:17][CH:16]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.[NH2:24][C:25]1[C:26]2[CH:39]=[C:38]([C:40]([NH:42][N:43]([CH3:50])[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:41])[S:37][C:27]=2[N:28](C(OC(C)(C)C)=O)[N:29]=1>O1CCCC1>[CH3:50][N:43]([C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[NH:42][C:40]([C:38]1[S:37][C:27]2[NH:28][N:29]=[C:25]([NH:24][C:19](=[O:20])[C:18]3[CH:22]=[CH:23][C:15]([CH2:14][N:8]4[CH2:13][CH2:12][O:11][CH2:10][CH2:9]4)=[CH:16][CH:17]=3)[C:26]=2[CH:39]=1)=[O:41]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 217058624-[(Morpholin-4-yl)methyl]benzoyl chloride--hydrogen chloride (1/1)HCID 57848800HCID 57848800, compound

Product 1

HCID 178486249HCID 178486249, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

193 mg (1.39 mmol) of potassium carbonate, followed by 240 mg (0.87 mmol) of 4-morpholin-4-ylmethylbenzoyl chloride hydrochloride, 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 a temperature in the region of 25° C. for 2 hours, and then refluxed for 4 hours. The reaction mixture is then cooled to a temperature in the region of 25° C., and then 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 40° C. The residue is purified by chromatography on a cartridge of 25 g of silica gel (0.015-0.040 mm), eluting successively with pure dichloromethane, and then with dichloromethane/methanol mixtures (99/1 by volume, and then 98.5/1.5, 98/2 and finally 97/3) at a flow rate of 10 mL/min. The fractions containing the expected product are combined and then concentrated to dryness under reduced pressure (0.6 kPa) at a temperature in the region of 30° C. 0.1 g of N-[5-(N′-methyl-N′-phenylhydrazinocarbonyl)-1H-thieno[2,3-c]pyrazol-3-yl]-4-morpholin-4-ylmethylbenzamide is thus obtained in the form of an off-white solid melting at 190° C.

Workup

  1. temperaturerefluxed for 4 hours
  2. temperatureThe reaction mixture is then cooled to a temperature in the region of 25° C.
  3. extractionThe mixture is extracted successively with 60 mL
  4. washwashed twice with 40 mL of saturated brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under vacuum (2 kPa) at a temperature in the region of 40° C
  8. customThe residue is purified by chromatography on a cartridge of 25 g of silica gel (0.015-0.040 mm)
  9. washeluting successively with pure dichloromethane
  10. additionThe fractions containing the expected product
  11. concentrationconcentrated to dryness under reduced pressure (0.6 kPa) at a temperature in the region of 30° C

Sources & evidence

ORD record
ord-9a156ee2de994e15be5f1d2214a31573
Source dataset
uspto-grants-2009_09
Patent number
US07595320B2

Reaction notes

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