Potassium Carbonate → HCID 10451188, compound

HRID 1244257Notes

Reaction equation

HRID 1244257 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH2:8]Cl)=[C:4]([N:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[CH:3]=1.[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[NH:23][CH:24]=[CH:25][N:26]=2)[N:17]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[N:7]=[N:6][C:5]([CH2:8][N:26]2[CH:25]=[CH:24][N:23]=[C:22]2[C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([F:15])[N:17]=2)=[C:4]([N:10]([CH2:13][CH3:14])[CH2:11][CH3:12])[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21919282HCID 21919282, compoundHCID 219192862-Fluoro-6-(1h-imidazol-2-yl)pyridine

Product 1

HCID 10451188HCID 10451188, compoundYield 22.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (6-chloro-3-chloromethyl-pyridazin-4-yl)-diethyl-amine (crude, 180 mg, 0.77 mmol), 2-fluoro-6-(1H-imidazol-2-yl)-pyridine (78 mg, 0.48 mmol) and K2CO3 (330 mg, 2.4 mmol) in DMF (5 mL) is stirred at room temperature overnight. The reaction is quenched with brine (4 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers are dried and solvent removed. PTLC separation (10% MeOH in DCM) gives 39 mg of {6-chloro-3-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-pyridazin-4-yl}-diethyl-amine as a solid. 1H NMR (CDCl3) 8.12 dd, 1H), 7.90 (dd, 1H), 7.19 (s, 1H), 7.07 (s, 1H), 6.79 (s, 1H), 6.77 (dd, 1H), 6.04 (s, 2H), 3.28 (q, 4H), 1.17 (t, 6H).

Workup

  1. customThe reaction is quenched with brine (4 mL)
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. customThe combined organic layers are dried
  4. customsolvent removed
  5. customPTLC separation (10% MeOH in DCM)

Sources & evidence

ORD record
ord-7c100df169c74bc4a4ecb21eb7e60348
Source dataset
uspto-grants-2006_10
Patent number
US07122546B2

Reaction notes

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