4-Aminopyridine → 3-(Methylsulfanyl)-5-[(pyridin-4-yl)amino]-1,2-thiazole-4-carbonitrile

HRID 1178698Notes

Reaction equation

HRID 1178698 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[CH3:14][S:15][C:16]1[C:20]([C:21]#[N:22])=[C:19](SC)[S:18][N:17]=1.[Cl-].[NH4+]>C1COCC1.O>[CH3:14][S:15][C:16]1[C:20]([C:21]#[N:22])=[C:19]([NH:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=2)[S:18][N:17]=1

Participants

7

Reactant 4

HCID 17274-AminopyridineHCID 25517Ammonium ChlorideHCID 3056313,5-Bis(methylsulfanyl)-1,2-thiazole-4-carbonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 695154203-(Methylsulfanyl)-5-[(pyridin-4-yl)amino]-1,2-thiazole-4-carbonitrileYield 81.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-aminopyridine (930 mg, 9.9 mmol) is dissolved in anhydrous THF (30 mL) and potassium tertbutoxide (1.11 g, 9.9 mmol) is added. The resulting solution is stirred for 1 hour at room temperature. 3,5-Bis-methylsulfanyl-isothiazole-4-carbonitrile (6) (1.0 g, 4.94 mmol) is added and the reaction is stirred for 3 days. Ammonium chloride (173 mg, 9.9 mmol) is added and the resulting suspension is stirred at room temperature for 30 min. A small amount of water is added and the solution is filtered. The mother liquor is concentrated in vacuo. Chromatography (5% MeOH/methylene chloride) provides 7 (1.0g, 81%). 1H NMR (d6 DMSO): δ 8.29 (2H, broad s), 7.04 (2H, broad s), 2.60 (3H, s).

Workup

  1. stirringthe reaction is stirred for 3 days
  2. stirringthe resulting suspension is stirred at room temperature for 30 min
  3. filtrationthe solution is filtered
  4. concentrationThe mother liquor is concentrated in vacuo

Sources & evidence

ORD record
ord-80b31d9f3bf04af58142dee978cb7054
Source dataset
uspto-grants-2007_10
Patent number
US07276602B2

Reaction notes

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