1-Methylhomopiperazine → HCID 178480451, compound

HRID 736267Notes

Reaction equation

HRID 736267 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3]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>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][N:5]([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)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 2283491-MethylhomopiperazineHCID 57848822HCID 57848822, compoundHCID 57848870HCID 57848870, compound

Product 1

HCID 178480451HCID 178480451, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

27 mg (74 μmol) of tetrabutylammonium iodide, followed by 138 μL (1.11 mmol) of N-methyl-homopiperazine, 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 treated with ice. It is then extracted with ethyl acetate and twice with dichloromethane. The organic extracts are combined and then concentrated to dryness under vacuum (2 kPa) at a temperature in the region of 40° C. The residue is dissolved in 3 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 (1 injection: conditions B′; 3 injections: conditions B). 53 mg of 4-(4-methylperhydro-1,4-diazepin-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. LC-MS-DAD-ELSD: 516(−)=(M−H)(−); 518(+)=(M+H)(+).

Workup

  1. additiontreated with ice
  2. extractionIt is then extracted with ethyl acetate and twice with dichloromethane
  3. concentrationconcentrated to dryness under vacuum (2 kPa) at a temperature in the region of 40° C
  4. dissolutionThe residue is dissolved in 3 mL of methanol
  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 30 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 (1 injection

Sources & evidence

ORD record
ord-d5292588241146c0864a6401528d79a9
Source dataset
uspto-grants-2009_09
Patent number
US07595320B2

Reaction notes

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