Ethyl orthopropionate → ethyl 4-(8-ethyl-5,6-dimethyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl)butanoate

HRID 2366704Notes

Reaction equation

HRID 2366704 reaction equation
Cl.N1C=C[CH:5]=[CH:4][CH:3]=1.C(OCC)(OCC)(OCC)CC.[NH2:20][C:21]1[C:22]2[N:23]([N:38]=[N:39][N:40]=2)[C:24]([CH3:37])=[C:25]([CH3:36])[C:26]=1[NH:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32]>C1(C)C=CC=CC=1>[CH2:4]([C:5]1[N:27]([CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32])[C:26]2[C:25]([CH3:36])=[C:24]([CH3:37])[N:23]3[N:38]=[N:39][N:40]=[C:22]3[C:21]=2[N:20]=1)[CH3:3]

Participants

5

Reactant 3

HCID 66995Ethyl orthopropionateHCID 10176127Pyridinium chlorideHCID 57447079Ethyl 4-[(8-amino-5,6-dimethyltetraazolo[1,5-a]pyridin-7-yl)amino]butanoate

Product 1

HCID 69506826ethyl 4-(8-ethyl-5,6-dimethyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl)butanoateYield 246.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

For Examples 42 and 43, pyridine hydrochloride (668 mg, 5.78 mmol) and triethyl orthopropionate (3.4 mL, 17 mmol) were added to a solution of ethyl 4-[(8-amino-5,6-dimethyltetraazolo[1,5-a]pyridin-7-yl)amino]butanoate (4.5 g, 15 mmol) in toluene (100 mL). The reaction and work-up procedure were as described for Examples 40 and 41. The crude product was recrystallized from ethyl acetate:hexane, isolated by filtration, washed with ethyl acetate:hexane, and dried under high vacuum to provide 4.7 g of ethyl 4-(8-ethyl-5,6-dimethyl-7H-imidazo[4,5-c]tetraazolo[1,5-a]pyridin-7-yl)butanoate as off-white crystals.

Workup

  1. customThe reaction
  2. customThe crude product was recrystallized from ethyl acetate
  3. customhexane, isolated by filtration
  4. washwashed with ethyl acetate
  5. dry with materialhexane, and dried under high vacuum

Sources & evidence

ORD record
ord-995025c20d1141aa8318a87c3d8ac9c2
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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