Trimethyl orthoacetate → HCID 21914058, compound

HRID 1352563Notes

Reaction equation

HRID 1352563 reaction equation
Cl.N1C=CC=[CH:4][CH:3]=1.C(OC)(OC)(OC)C.[Cl:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]1[C:28]([CH3:29])=[C:27]([CH3:30])[N:26]=[C:25]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:24]=1[NH2:38]>O1CCCC1.C(OCC)(=O)C>[Cl:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[C:23]2[C:28]([CH3:29])=[C:27]([CH3:30])[N:26]=[C:25]([O:31][C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:24]=2[N:38]=[C:3]1[CH3:4]

Participants

6

Reactant 3

HCID 15050Trimethyl orthoacetateHCID 10176127Pyridinium chlorideHCID 85898859HCID 85898859, compound

Product 1

HCID 21914058HCID 21914058, compoundYield 340.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Pyridine hydrochloride (2 g) and trimethyl orthoacetate (10.5 mL, 82 mmol) were added to a solution of N4-(5-chloropentyl)-5,6-dimethyl-2-phenoxypyridine-3,4-diamine (24.97 g, 75 mmol) in anhydrous tetrahydrofuran (200 mL). The reaction mixture was heated at reflux for 25 hours, cooled to ambient temperature and then concentrated under reduced pressure. The residue was dissolved in hot ethyl acetate, titrated with hexanes and then cooled. The resulting precipitate was isolated by filtration and then it was dissolved in ethyl acetate (300 mL), washed with water (2×100 mL) and with brine (1×100 mL), dried over magnesium sulfate and then concentrated under reduced pressure to provide 21.09 g of 1-(5-chloropentyl)-2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridine.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 25 hours
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe residue was dissolved in hot ethyl acetate
  5. temperaturecooled
  6. customThe resulting precipitate was isolated by filtration
  7. washwashed with water (2×100 mL) and with brine (1×100 mL)
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6aa633c03e6d4020988ae3384e8c2c8d
Source dataset
uspto-grants-2007_05
Patent number
US07220758B2

Reaction notes

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