Butyric Acid → 5-Butyramido-2-propylimidazo[4,5-b]pyridine

HRID 466688

Reaction equation

HRID 466688 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[C:4]([NH2:11])[N:3]=1.[C:12]([OH:17])(=O)[CH2:13][CH2:14][CH3:15].C(Cl)Cl>CO.O.[NH4+].[OH-].[Pd]>[C:12]([NH:11][C:4]1[N:3]=[C:2]2[N:1]=[C:4]([CH2:5][CH2:6][CH3:7])[NH:8][C:7]2=[CH:6][CH:5]=1)(=[O:17])[CH2:13][CH2:14][CH3:15]

Participants

8

Reactant 3

HCID 264Butyric AcidHCID 6344DichloromethaneHCID 3199982,6-Diamino-3-nitropyridine

Product 1

HCID 224073815-Butyramido-2-propylimidazo[4,5-b]pyridineYield 49.1%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2,6-diamino-3-nitropyridine (878 mg, 5.7 mmol) and Pd-C (10%, 100 mg) in MeOH (100 mL) was stirred under 1 atm. H2 for 16 hours. The mixture (containing the air sensitive triamine) was filtered, evaporated, and to this flask was added polyphosphoric acid (15 mL) and butyric acid (1.05 mL, 11.5 mmol). This mixture was heated to 80° C. for 5 hours, cooled to room temperature, diluted with water and neutralized with concentrated NH4OH. Extractive workup (CH2Cl2) gave 345 mg of 5-(butyramido)-2-propylimidazo[4,5-b]pyridine.

Workup

  1. filtrationwas filtered
  2. customevaporated
  3. temperaturecooled to room temperature

Sources & evidence

ORD record
ord-456bbe93220848599009a8d9c9554856
Source dataset
uspto-grants-1992_10
Patent number
US05157026

Linked notes

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