Trimethyl orthoacetate → [2,5-Dimethyl-3-(2,4,6-trimethyl-phenyl)-3H-imidazo[4,5-b]pyridin-7-yl]-(1-ethyl-propyl)-amine

HRID 1245749Notes

Reaction equation

HRID 1245749 reaction equation
[CH2:1]([CH:3]([NH:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([NH:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[C:8]=1[NH2:24])[CH2:4][CH3:5])[CH3:2].[C:25](OC)(OC)(OC)[CH3:26].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:25][C:26]1[N:14]([C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[C:9]2=[N:10][C:11]([CH3:13])=[CH:12][C:7]([NH:6][CH:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[C:8]2[N:24]=1

Participants

5

Reactant 3

HCID 15050Trimethyl orthoacetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 21912187N4-(1-ethyl-propyl)-6-methyl-N2-(2,4,6-trimethyl-phenyl)-pyridine-2,3,4-triamine

Product 1

HCID 21912040[2,5-Dimethyl-3-(2,4,6-trimethyl-phenyl)-3H-imidazo[4,5-b]pyridin-7-yl]-(1-ethyl-propyl)-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of N4-(1-ethyl-propyl)-6-methyl-N2-(2,4,6-trimethyl-phenyl)-pyridine-2,3,4-triamine (250 mg, 0.77 mmol), trimethyl orthoacetate (0.184 g, 1.532 mmol), p-toluenesulfonic acid monohydrate (0.01 g) in toluene was heated at reflux using Dean-Stark apparatus for 3 hours. The mixture was quenched with water, brine, extracted with ethyl acetate. The organic layer was separated, dried (MgSO4) and concentrated to dryness. After purification, the title compound was obtained as a white crystal, mp 101–103° C. Anal. For C22H30N4 calc. C, 75.39; H, 8.63; N, 15.98; found, C, 75.44; H, 8.95; N, 15.95.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customfor 3 hours
  4. customThe mixture was quenched with water, brine
  5. extractionextracted with ethyl acetate
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated to dryness
  9. customAfter purification

Sources & evidence

ORD record
ord-6ee143ff6e1d434daeac3a462b57b1a1
Source dataset
uspto-grants-2006_10
Patent number
US07125880B1

Reaction notes

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