Ethyl Acetate → HCID 178430317, compound

HRID 736266Notes

Reaction equation

HRID 736266 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][C@@H:4]([CH3:8])[NH:3]1.Cl[CH2:10][C:11]1[CH:45]=[CH:44][C:14]([C:15]([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(OC(C)(C)C)=O)[N:22]=2)=[O:16])=[CH:13][CH:12]=1.ClCC1C=CC(C(NC2C3C=C(C(NN(C4C=CC(Cl)=CC=4)C)=O)SC=3N(C(OC(C)(C)C)=O)N=2)=O)=CC=1.C(OCC)(=O)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.CO.CCCCCCC>[CH3:8][CH:4]1[NH:3][CH:2]([CH3:1])[CH2:7][N:6]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([NH:17][C:18]3[C:19]4[CH:32]=[C:31]([C:33]([NH:35][N:36]([CH3:43])[C:37]5[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=5)=[O:34])[S:30][C:20]=4[NH:21][N:22]=3)=[O:16])=[CH:44][CH:45]=2)[CH2:5]1

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 57848822HCID 57848822, compoundHCID 57848870HCID 57848870, compound

Product 1

HCID 178430317HCID 178430317, compound

Reagents, catalysts & solvents 4

HCID 67553Tetrabutylammonium IodideCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8900HeptaneSolvent

Conditions

Temperature
25 °C

Procedure

40 mg (108 μmol) of tetrabutylammonium iodide, followed by 184 mg (1.61 mmol) of cis-2,6-dimethylpiperazine, are added to a solution of 290 mg (0.54 mmol) of an approximately 70:30 mixture of tert-butyl 3-(4-chloromethylbenzoylamino)-5-(N′-methyl-N′-phenylhydrazinocarbonyl)thieno[2,3-c]pyrazole-1-carboxylate and tert-butyl 3-(4-chloromethylbenzoylamino)-5-(N′-(4-chlorophenyl)-N′-methylhydrazinocarbonyl)thieno[2,3-c]pyrazole-1-carboxylate in 6 mL of dimethylformamide under argon. The reaction mixture is stirred at a temperature in the region of 25° C. for 3 hours, and then poured into a mixture of ice, ethyl acetate and n-heptane. The mixture is filtered on a sinter funnel, suction-filtered and air-dried. The solid obtained is dissolved in 5 mL of methanol and the solution is introduced into a microwave oven tube. The tube is stoppered and the reaction mixture is irradiated at a temperature in the region of 100° C. for three times 10 minutes. The reaction mixture is then concentrated to dryness under vacuum (2 kPa) at a temperature in the region of 40° C. The residue is purified by preparative LC/MS (condition B′). 130 mg of 4-(3,5-dimethylpiperazin-1-ylmethyl)-N-[5-(N′-methyl-N′-phenylhydrazinocarbonyl)-1H-thieno[2,3-c]pyrazol-3-yl]benzamide are thus obtained in the form of a yellow powder melting between 192 and 202° C. LC-MS-DAD-ELSD: 518(+)=(M+H)(+).

Workup

  1. filtrationThe mixture is filtered on a sinter funnel
  2. filtrationsuction-filtered
  3. customair-dried
  4. customThe solid obtained
  5. additionthe solution is introduced into a microwave oven tube
  6. customthe reaction mixture is irradiated at a temperature in the region of 100° C. for three times 10 minutes
  7. concentrationThe reaction mixture is then concentrated to dryness under vacuum (2 kPa) at a temperature in the region of 40° C
  8. customThe residue is purified by preparative LC/MS (condition B′)

Sources & evidence

ORD record
ord-18448112d4534a959a51ae173e38d0a6
Source dataset
uspto-grants-2009_09
Patent number
US07595320B2

Reaction notes

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