Potassium Carbonate → HCID 85472988, compound

HRID 1471716Notes

Reaction equation

HRID 1471716 reaction equation
[OH:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([O:10][CH3:11])=[N:4][CH:3]=1.Cl.Cl[CH2:14][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[C:21]1[N:25]([CH:26]([CH3:28])[CH3:27])[N:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH:26]([N:25]1[C:21]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][C:15]=2[CH2:14][O:1][C:2]2[C:7]([CH:8]=[O:9])=[CH:6][C:5]([O:10][CH3:11])=[N:4][CH:3]=2)=[CH:22][CH:23]=[N:24]1)([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 722124985-Hydroxy-2-methoxyisonicotinaldehydeHCID 86690757HCID 86690757, compound

Product 1

HCID 85472988HCID 85472988, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-hydroxy-2-methoxyisonicotinaldehyde (79 mg, 0.52 mmol, 1.5 eq.), 4-(chloromethyl)-3-(1-isopropyl-1H-pyrazol-5-yl)pyridine hydrochloride (crude above, 0.35 mmol), and K2CO3 (145 mg, 1.05 mmol, 3 eq.) in DMF (10.0 mL) was heated at 100° C. for 2 h. The mixture was cooled, filtered, concentrated, and purified on RP-HPLC (Gemini 21.2×150 mm) twice using a mixture of CH3CN/water (0.1% HCOOH) as eluent to give 5-((3-(1-isopropyl-1H-pyrazol-5-yl)pyridin-4-yl)methoxy)-2-methoxyisonicotinaldehyde (6.0 mg, 5%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 10.29 (s, 1H), 8.63 (s, 1H), 8.42 (s, 1H), 7.67 (s, 1H), 7.54 (s, 1H), 7.52 (d, J=1.7 Hz, 1H), 6.96 (s, 1H), 6.15 (d, J=1.8 Hz, 1H), 4.87 (s, 2H), 4.06 (sep, J=6.6 Hz, 1H), 3.75 (s, 3H), 1.31 (d, J=6.6 Hz, 6H). LRMS (M+H+) m/z 353.1.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. custompurified on RP-HPLC (Gemini 21.2×150 mm)
  5. additiona mixture of CH3CN/water (0.1% HCOOH) as eluent

Sources & evidence

ORD record
ord-6825244d585c4312a74252105628f1ec
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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