Potassium Carbonate → HCID 178486242, compound

HRID 736262Notes

Reaction equation

HRID 736262 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:42]=[CH:41][C:11]([C:12]([NH:14][C:15]2[C:16]3[CH:29]=[C:28]([C:30]([NH:32][N:33]([CH3:40])[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:31])[S:27][C:17]=3[N:18](C(OC(C)(C)C)=O)[N:19]=2)=[O:13])=[CH:10][CH:9]=1>CO>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([C:12]([NH:14][C:15]2[C:16]3[CH:29]=[C:28]([C:30]([NH:32][N:33]([CH3:40])[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)=[O:31])[S:27][C:17]=3[NH:18][N:19]=2)=[O:13])=[CH:41][CH:42]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 57848813HCID 57848813, compound

Product 1

HCID 178486242HCID 178486242, compoundYield 54.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

14.5 mg (105 μmol) of potassium carbonate are added to a solution of 0.04 g (70 μmol) of tert-butyl 3-(4-bromobenzoylamino)-5-(N′-methyl-N′-phenylhydrazinocarbonyl)thieno[2,3-c]pyrazole-1-carboxylate in 3 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 (2 kPa) at a temperature in the region of 35° C. The residue is taken up in dichloromethane, and then in a mixture of 1 mL of methanol, 4 mL of water and 10 mL of ethyl acetate. After separation of the phases by settling, the organic phase is washed twice with 3 mL of water, 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 taken up in diisopropyl ether, filtered on a sinter funnel, suction-filtered and then dried in an oven under vacuum (0.01 kPa) at a temperature in the region of 40° C. The residue is purified by chromatography on a column of 15 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 20 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. 18 mg of 4-bromo-N-[5-(N′-methyl-N′-phenylhydrazinocarbonyl)-1H-thieno[2,3-c]pyrazol-3-yl]benzamide are thus obtained in the form of a pale yellow solid melting at 172° C. LC-MS-DAD-ELSD: 468(−)/ . . . =(M−H)(−)/ . . . ; 470(+)/ . . . =(M+H)(+)/ . . . (1 Br present).

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 (2 kPa) at a temperature in the region of 35° C
  3. additionin a mixture of 1 mL of methanol, 4 mL of water and 10 mL of ethyl acetate
  4. customAfter separation of the phases
  5. washthe organic phase is washed twice with 3 mL of water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under vacuum (2 kPa) at a temperature in the region of 35° C
  9. filtrationfiltered on a sinter funnel
  10. filtrationsuction-filtered
  11. customdried in an oven under vacuum (0.01 kPa) at a temperature in the region of 40° C
  12. customThe residue is purified by chromatography on a column of 15 g of silica gel (0.015-0.040 mm)
  13. washeluting with a dichloromethane/methanol mixture (99/1 by volume
  14. additionThe fractions containing the expected product
  15. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 35° C

Sources & evidence

ORD record
ord-04e47994c41a4168b3dfc6aca85f48ef
Source dataset
uspto-grants-2009_09
Patent number
US07595320B2

Reaction notes

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