Potassium Carbonate → HCID 178486249, compound

HRID 736258Notes

Reaction equation

HRID 736258 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][N:8]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[NH:9][C:10]([C:12]1[S:42][C:15]2[N:16](C(OC(C)(C)C)=O)[N:17]=[C:18]([NH:19][C:20](=[O:34])[C:21]3[CH:26]=[CH:25][C:24]([CH2:27][N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[CH:23][CH:22]=3)[C:14]=2[CH:13]=1)=[O:11]>CO>[CH3:7][N:8]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[NH:9][C:10]([C:12]1[S:42][C:15]2[NH:16][N:17]=[C:18]([NH:19][C:20](=[O:34])[C:21]3[CH:22]=[CH:23][C:24]([CH2:27][N:28]4[CH2:29][CH2:30][O:31][CH2:32][CH2:33]4)=[CH:25][CH:26]=3)[C:14]=2[CH:13]=1)=[O:11]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57848855HCID 57848855, compound

Product 1

HCID 178486249HCID 178486249, compoundYield 52.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

21 mg (154 μmol) of potassium carbonate are added to a solution of 0.09 g (154 μmol) of tert-butyl 5-(N′-methyl-N′-phenylhydrazinocarbonyl)-3-(4-morpholin-4-ylmethylbenzoylamino)thieno[2,3-c]pyrazole-1-carboxylate in 5 mL of methanol in a microwave oven tube. The tube is stoppered and the reaction mixture is irradiated at a temperature in the region of 180° C. for 3 minutes. The reaction mixture is then concentrated to dryness under vacuum (0.6 kPa) at a temperature in the region of 30° C. The residue is purified by chromatography on a cartridge of 25 g of silica gel (0.015-0.040 mm), eluting with a dichloromethane/methanol mixture (99/1 by volume, then 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 (1.0 kPa) at a temperature in the region of 30° C. The residue is taken up in 10 mL of diisopropyl ether, triturated and then reconcentrated to dryness. The solid obtained is dried in an oven under vacuum (0.01 kPa) at a temperature in the region of 60° C. 40 mg of N-[5-(N′-methyl-N′-phenylhydrazinocarbonyl)-1H-thieno[2,3-c]pyrazol-3-yl]-4-morpholin-4-ylmethylbenzamide are thus obtained in the form of an off-white solid melting at 242° C. MS-EI: 490(+)=M(+).

Workup

  1. customthe reaction mixture is irradiated at a temperature in the region of 180° C. for 3 minutes
  2. concentrationThe reaction mixture is then concentrated to dryness under vacuum (0.6 kPa) at a temperature in the region of 30° C
  3. customThe residue is purified by chromatography on a cartridge of 25 g of silica gel (0.015-0.040 mm)
  4. washeluting with a dichloromethane/methanol mixture (99/1 by volume
  5. additionThe fractions containing the expected product
  6. concentrationconcentrated to dryness under reduced pressure (1.0 kPa) at a temperature in the region of 30° C
  7. customtriturated
  8. customThe solid obtained
  9. customis dried in an oven under vacuum (0.01 kPa) at a temperature in the region of 60° C

Sources & evidence

ORD record
ord-c01c50f4e76b40808cfdd79a0794b846
Source dataset
uspto-grants-2009_09
Patent number
US07595320B2

Reaction notes

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