1,2-Ethanediamine, N1,N1,N2-trimethyl- → HCID 178483774, compound

HRID 736274Notes

Reaction equation

HRID 736274 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][NH:5][CH3:6].Cl[CH2:9][C:10]1[CH:44]=[CH:43][C:13]([C:14]([NH:16][C:17]2[C:18]3[CH:31]=[C:30]([C:32]([NH:34][N:35]([CH3:42])[C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[O:33])[S:29][C:19]=3[N:20](C(OC(C)(C)C)=O)[N:21]=2)=[O:15])=[CH:12][CH:11]=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>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][N:5]([CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:14]([NH:16][C:17]2[C:18]3[CH:31]=[C:30]([C:32]([NH:34][N:35]([CH3:42])[C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)=[O:33])[S:29][C:19]=3[NH:20][N:21]=2)=[O:15])=[CH:43][CH:44]=1)[CH3:6]

Participants

6

Reactant 3

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 57848822HCID 57848822, compoundHCID 57848870HCID 57848870, compound

Product 1

HCID 178483774HCID 178483774, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

27 mg (74 μmol) of tetrabutylammonium iodide and then 144 μL (1.11 mmol) of N,N,N′-trimethylethylenediamine are added to a solution of 200 mg (0.37 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 16 hours and then poured onto ice. It is then extracted twice with a 50/50 mixture of ethyl acetate and heptane. The organic extracts are combined, dried over magnesium sulfate and then concentrated to dryness under vacuum (2 kPa) at a temperature in the region of 40° C. The residue is dissolved in 4 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 30 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 (conditions B). 40 mg of 4-{[(2-dimethylaminoethyl)methylamino]methyl}-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. LC-MS-DAD-ELSD: 506(+)=(M+H)(+).

Workup

  1. additionpoured onto ice
  2. extractionIt is then extracted twice with a 50/50 mixture of ethyl acetate and heptane
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to dryness under vacuum (2 kPa) at a temperature in the region of 40° C
  5. dissolutionThe residue is dissolved in 4 mL of methanol
  6. additionthe solution is introduced into a microwave oven tube
  7. customthe reaction mixture is irradiated at a temperature in the region of 100° C. for 30 minutes
  8. concentrationThe reaction mixture is then concentrated to dryness under vacuum (2 kPa) at a temperature in the region of 40° C
  9. customThe residue is purified by preparative LC/MS (conditions B)

Sources & evidence

ORD record
ord-1ee5ca3e5e6d480da59042a59ba4cf13
Source dataset
uspto-grants-2009_09
Patent number
US07595320B2

Reaction notes

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