Dichloromethane → Imidazo[2,1-b]thiazole,5-ethyl-6-[[2-(6-fluoro-2-pyridinyl)-1h-imidazol-1-yl]methyl]-

HRID 586379Notes

Reaction equation

HRID 586379 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]2[N:9]([C:10]=1[CH2:11][CH3:12])[CH:8]=[CH:7][S:6]2.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[NH:21][CH:22]=[CH:23][N:24]=2)[N:15]=1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>CN(C=O)C.[Cl-].[Na+].O>[CH2:11]([C:10]1[N:9]2[C:5]([S:6][CH:7]=[CH:8]2)=[N:4][C:3]=1[CH2:2][N:24]1[CH:23]=[CH:22][N:21]=[C:20]1[C:16]1[CH:17]=[CH:18][CH:19]=[C:14]([F:13])[N:15]=1)[CH3:12]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 219192862-Fluoro-6-(1h-imidazol-2-yl)pyridineHCID 223351136-Chloromethyl-5-ethyl-imidazo[2,1-b]thiazole

Product 1

HCID 22335063Imidazo[2,1-b]thiazole,5-ethyl-6-[[2-(6-fluoro-2-pyridinyl)-1h-imidazol-1-yl]methyl]-Yield 16.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 6-chloromethyl-5-ethyl-imidazo[2,1-b]thiazole (120 mg, 0.6 mmol), 2-fluoro-6-(1H-imidazol-2-yl)pyridine (82 mg, 0.6 mmol) and potassium carbonate (278 mg, 2.4 mmol) in DMF (6 mL) is stirred at room temperature for 48 h. Brine (15 mL) and methylene chloride (20 mL) are added. The organic layer is separated and the aqueous layer is extracted with methylene chloride (2×20 mL). The combined organic layers are washed with brine (3×15 mL) and dried. The solvent is removed in vacuo. The residue is purified by preparative TLC to give 32 mg of 5-ethyl-6-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-imidazo[2,1-b]thiazole as an oil. 1H NMR (CDCl3): 8.10, dd (1H); 7.82, dd (1H); 7.35, d (1H); 7.26, d (1H); 7.12, d (1H); 6.83, dd (1H); 6.80, d (1H); 5.92, s (2H); 2.90, q (2H); 1.07, t (3H).

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous layer is extracted with methylene chloride (2×20 mL)
  3. washThe combined organic layers are washed with brine (3×15 mL)
  4. customdried
  5. customThe solvent is removed in vacuo
  6. customThe residue is purified by preparative TLC

Sources & evidence

ORD record
ord-c6adbdbc22724a6c988dd54e663d2beb
Source dataset
uspto-grants-2005_08
Patent number
US06936617B2

Reaction notes

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