Potassium Carbonate → HCID 24968709, compound

HRID 655294Notes

Reaction equation

HRID 655294 reaction equation
[S:1]1[C:5]2[CH:6]=[C:7]([CH2:10][C:11](O)=O)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[Cl:14][C:15]1[N:20]=[N:19][C:18]([NH:21][NH2:22])=[CH:17][CH:16]=1.Cl.CN(C)CCCN=C=NCC.O.OC1C2N=NNC=2C=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.ClCCl.C(O)(=O)C>[S:1]1[C:5]2[CH:6]=[C:7]([CH2:10][C:11]3[N:19]4[N:20]=[C:15]([Cl:14])[CH:16]=[CH:17][C:18]4=[N:21][N:22]=3)[CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 1007873-Chloro-6-hydrazinopyridazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22038417(1,3-Benzothiazol-6-yl)acetic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 24968709HCID 24968709, compoundYield 21.8%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Benzothiazol-6-yl-acetic acid (44 g, 228 mmoles) and (6-chloro-pyridazin-3-yl)-hydrazine (36.2 g, 251 mmoles) were dissolved in a mixture of anhydrous dimethylformamide (40 mL) and anhydrous dichloromethane (600 ml). The mixture was under nitrogen and cooled to 0° C. in an ice bath, then N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (65.5 g, 342 mmoles), hydroxybenzotriazole hydrate (38.4 g, 251 mmoles) and potassium carbonate (157 g, 1.14 moles) was added into the mixture. The mixture was stirred at 5° C. for 4 h and at room temperature overnight. TLC showed that the SM disappeared. The mixture was filtered and the filtrate was washed with brine (400 mL×2). The organic phase was dried over anhydrous Na2SO4, concentrated to obtain a brown oil. The oil was dissolved in acetic acid (750 mL) and stirred at 50° C. for 4 hours. After such time the solvent was removed in vacuo and the residue was purified by a silica gel column eluting with ethyl acetate to obtain crude product (20 g). The crude product was recrystallized from ethyl acetate and petroleum ether to obtain the title compound (15 g). Analytical data presented in Table 1.

Workup

  1. filtrationThe mixture was filtered
  2. washthe filtrate was washed with brine (400 mL×2)
  3. dry with materialThe organic phase was dried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customto obtain a brown oil
  6. stirringstirred at 50° C. for 4 hours
  7. customAfter such time the solvent was removed in vacuo
  8. customthe residue was purified by a silica gel column
  9. washeluting with ethyl acetate
  10. customto obtain crude product (20 g)
  11. customThe crude product was recrystallized from ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-8dda8eb5c71a4709a3a6b1a110c234da
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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