Potassium Carbonate → HCID 24964085, compound

HRID 655277Notes

Reaction equation

HRID 655277 reaction equation
Cl.Cl.[C:3]1([C:9]2[N:14]=[N:13][C:12]([NH:15][NH2:16])=[CH:11][CH:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([CH2:28][C:29](O)=O)[CH:24]=2)[N:19]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:17][C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[C:23]([CH2:28][C:29]3[N:13]4[N:14]=[C:9]([C:3]5[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=5)[CH:10]=[CH:11][C:12]4=[N:15][N:16]=3)[CH:24]=2)[N:19]=1

Participants

7

Reactant 5

HCID 11430Potassium CarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59320364HCID 59320364, compoundHCID 68705560Pyridazine, 3-hydrazinyl-6-phenyl-, hydrochloride (1:2)

Product 1

HCID 24964085HCID 24964085, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A vial was charged with (6-phenyl-pyridazin-3-yl)-hydrazine dihydrochloride (20 mg, 0.077 mmol), (2-methyl-quinolin-6-yl)-acetic acid (17 mg, 0.085 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (22 mg, 0.115 mmol), 1-hydroxybenzotriazole hydrate (11 mg, 0.077 mmol), potassium carbonate (32 mg, 0.231 mmol), and N,N-dimethyl formamide (0.7 mL). The reaction mixture was stirred at room temperature for 14 h. After such time the mixture was concentrated in vacuo. Acetic acid (1 mL) was added to the residue and the resulting reaction mixture was stirred at 55° C. for 5 h. After such time the mixture was concentrated in vacuo and partitioned between 1 M aqueous potassium carbonate and ethyl acetate. The organic layer was washed with 1 M aqueous potassium carbonate, then brine, and directly adsorbed on silica gel. Purification on silica gel with 0-8% gradient of methanol in ethyl acetate afforded the title compound (8.7 mg, 0.024 mmol, 32% yield) as a light yellow solid. Analytical data presented in Table 1.

Workup

  1. concentrationAfter such time the mixture was concentrated in vacuo
  2. additionAcetic acid (1 mL) was added to the residue
  3. customthe resulting reaction mixture
  4. stirringwas stirred at 55° C. for 5 h
  5. concentrationAfter such time the mixture was concentrated in vacuo
  6. custompartitioned between 1 M aqueous potassium carbonate and ethyl acetate
  7. washThe organic layer was washed with 1 M aqueous potassium carbonate
  8. customPurification on silica gel with 0-8% gradient of methanol in ethyl acetate

Sources & evidence

ORD record
ord-0c51c7547dd748938aea0bd0ba7eb37c
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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