Potassium Bicarbonate → HCID 178491889, compound

HRID 2044323Notes

Reaction equation

HRID 2044323 reaction equation
Cl.[Cl:2][C:3]1[C:8]([C:9]([NH2:11])=[NH:10])=[CH:7][N:6]=[C:5]([O:12][CH3:13])[CH:4]=1.C(=O)(O)[O-].[K+].Br[CH2:20][C:21]([C:23]1[N:24]([CH:29]([CH3:31])[CH3:30])[N:25]=[C:26]([CH3:28])[N:27]=1)=O>C1COCC1.O>[Cl:2][C:3]1[C:8]([C:9]2[NH:11][CH:20]=[C:21]([C:23]3[N:24]([CH:29]([CH3:31])[CH3:30])[N:25]=[C:26]([CH3:28])[N:27]=3)[N:10]=2)=[CH:7][N:6]=[C:5]([O:12][CH3:13])[CH:4]=1

Participants

6

Reactant 3

HCID 516893Potassium BicarbonateHCID 582048242-bromo-1-[3-methyl-1-(propan-2-yl)-1H-1,2,4-triazol-5-yl]ethan-1-oneHCID 670506614-Chloro-6-methoxynicotinimidamide hydrochloride

Product 1

HCID 178491889HCID 178491889, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 4-chloro-6-methoxy-nicotinamidine hydrochloride (18.4 mmol) and potassium bicarbonate (7.37 g, 73.6 mmol) in THF (42 mL) and water (8.5 mL) was heated to reflux and treated with a solution of 2-bromo-1-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-ethanone (4.53 g, 18.4 mmol) in THF (14 mL) added dropwise. The reaction mixture was heated at reflux for 18 h before removal of volatile solvent in vacuo. The resultant suspension was filtered and the residue washed with water then dried to give the title compound as a brown solid (5.91 g, 97%). LCMS: RT=2.68 min, [M+H]+=333/335. 1H NMR 400 MHz (CDCl3) δ: 10.41 (1H, s), 9.02 (1H, s), 7.81 (1H, s), 6.87 (1H, s), 5.91 (1H, m), 4.00 (3H, s), 2.41 (3H, s), 1.55 (6H, d, J=6.71 Hz).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. additionadded dropwise
  4. temperatureThe reaction mixture was heated
  5. temperatureat reflux for 18 h before removal of volatile solvent in vacuo
  6. filtrationThe resultant suspension was filtered
  7. washthe residue washed with water
  8. customthen dried

Sources & evidence

ORD record
ord-e4907dc933e648f190a909b6e3830af8
Source dataset
uspto-grants-2013_11
Patent number
US08586574B2

Reaction notes

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