Triethylamine → 1-isobutyl-4-[(4-methoxybenzyl)amino]-6,7-dimethyl-1H-imidazo[4,5-c]pyridine-2-carbaldehyde

HRID 2426371Notes

Reaction equation

HRID 2426371 reaction equation
[CH2:1]([N:5]1[C:13]2[C:12]([CH3:14])=[C:11]([CH3:15])[N:10]=[C:9]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[C:8]=2[N:7]=[C:6]1[CH2:26][OH:27])[CH:2]([CH3:4])[CH3:3].C(N(CC)CC)C.[Cl-].[NH4+]>ClCCl.CS(C)=O>[CH2:1]([N:5]1[C:13]2[C:12]([CH3:14])=[C:11]([CH3:15])[N:10]=[C:9]([NH:16][CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=3)[C:8]=2[N:7]=[C:6]1[CH:26]=[O:27])[CH:2]([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 67262962{1-Isobutyl-4-[(4-methoxybenzyl)amino]-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-2-yl}methanol

Product 1

HCID 866284411-isobutyl-4-[(4-methoxybenzyl)amino]-6,7-dimethyl-1H-imidazo[4,5-c]pyridine-2-carbaldehydeYield 92.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere {1-isobutyl-4-[(4-methoxybenzyl)amino]-6,7-dimethyl-1H-imidazo[4,5-c]pyridin-2-yl}methanol (2.00 g, 5.43 mmol, prepared as in Parts A-F of Example 9) was dissolved in dichloromethane (20 mL) and dimethylsulfoxide (10 mL). Triethylamine (2.27 mL, 16.3 mmol) was added and the solution was cooled to 0° C. Sulfur trioxide pyridine complex (2.60 g, 16.3 mmol) was then added in four portions and the solution was stirred at 0° C. for another 2 hours. The solution was then poured into saturated aqueous ammonium chloride (70 mL) and extracted with diethyl ether (3×80 mL). The organics were washed with water (2×30 mL) and brine (20 mL), dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give 1.84 g of 1-isobutyl-4-[(4-methoxybenzyl)amino]-6,7-dimethyl-1H-imidazo[4,5-c]pyridine-2-carbaldehyde as a yellow residue.

Workup

  1. additionSulfur trioxide pyridine complex (2.60 g, 16.3 mmol) was then added in four portions
  2. extractionextracted with diethyl ether (3×80 mL)
  3. washThe organics were washed with water (2×30 mL) and brine (20 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b82020ea07cc4d0b8aadec92ccb653e8
Source dataset
uspto-grants-2011_06
Patent number
US07968563B2

Reaction notes

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