Potassium Carbonate → HCID 57443120, compound

HRID 2262710Notes

Reaction equation

HRID 2262710 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11](=[O:19])[CH2:12][N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[Cl:20][C:21]1[N:22]=[N:23][C:24](Cl)=[CH:25][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[Cl:20][C:21]1[N:22]=[N:23][C:24]([N:16]2[CH2:15][CH2:14][N:13]([CH2:12][C:11]([N:8]3[CH2:9][CH2:10][N:5]([CH:1]4[CH2:2][CH2:3][CH2:4]4)[CH2:6][CH2:7]3)=[O:19])[CH2:18][CH2:17]2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 673313,6-DichloropyridazineHCID 57442330HCID 57442330, compound

Product 1

HCID 57443120HCID 57443120, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Dissolve 1-cyclobutyl-4-(piperazin-1-ylacetyl)piperazine (2.05 g, 5.46 mmol) and 3,6-dichloropyridazine (810 mg, 5.46 mmol) in dry DMSO (25 mL). Add K2CO3 (3.77 g, 27.3 mmol) and heat the mixture at 120° C. overnight. Cool and partition between CH2Cl2 (100 mL) and 1 N NaOH (150 mL). Extract the aqueous phase with CH2Cl2 (2×100 mL). Combine, dry and evaporate the organic extracts. Triturate the resulting residue with ether and filter off the solid (product). Evaporate the filtrate and chromatograph the resulting residue with EtOAc followed by EtOAc/MeOH (95:5) and EtOAc/MeOH/TEA(95:5:5) to yield additional product. 1H NMR (CDCl3) δ 7.21 (d, 1H), 6.89 (d, 1H), 3.68-3.59 (m, 8H), 3.22 (s, 2H), 2.78-2.62 (m, 5H), 2.38-2.28 (m, 4H), 2.13-2.03 (m, 2H), 1.93-1.8 (m, 2H), 1.73-1.69 (m, 2H); LC-MS (M+1) 378.98.

Workup

  1. temperatureCool
  2. custompartition between CH2Cl2 (100 mL) and 1 N NaOH (150 mL)
  3. extractionExtract the aqueous phase with CH2Cl2 (2×100 mL)
  4. customCombine, dry
  5. customevaporate the organic extracts
  6. customTriturate the resulting residue with ether
  7. filtrationfilter off the solid (product)
  8. customEvaporate the filtrate and chromatograph the resulting residue with EtOAc
  9. customto yield additional product

Sources & evidence

ORD record
ord-6bf5eb30237c41a39ef64abac19e470c
Source dataset
uspto-grants-2010_12
Patent number
US07851474B2

Reaction notes

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