Hydrochloric Acid → 3-[4-(benzyloxy)phenyl]-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 82632Notes

Reaction equation

HRID 82632 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:21]([NH2:22])=[C:20]([CH3:23])[CH:19]=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl.O.C1C[O:31][CH2:30]C1>>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:16]3=[N:17][CH:18]=[CH:19][C:20]([CH3:23])=[C:21]3[NH:22][C:30]2=[O:31])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58577506N2-[4-(benzyloxy)phenyl]-4-methylpyridine-2,3-diamine

Product 1

HCID 585772463-[4-(benzyloxy)phenyl]-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

Procedure

To a solution of N2-[4-(benzyloxy)phenyl]-4-methylpyridine-2,3-diamine (91.0 g) in THF (850 mL) was added N,N′-carbonylimidazol (90.8 g) at room temperature. The mixture was stirred at room temperature for 17 h. To the mixture was added 1 N NaOH (300 mL) over 10 min in ice bath, and the mixture was stirred for 15 min. To the mixture was added 1 N HCl (460 mL) under ice cooling, and then the mixture was stirred for 15 min. To the mixture was added water (90 mL) at room temperature, and then the mixture was stirred for 20 min. The precipitate was collected by filtration, washed with water (1.3 L), and dried in air blowing for 30 min. The precipitate was washed with IPE (1.5 L) and dried in vacuo at 55° C. for 2.5 h. The precipitate was suspended in IPE (500 mL), and the mixture was stirred at room temperature for 1 h. The precipitate was collected by filtration, washed with IPE (500 mL), and dried in vacuo to give 3-[4-(benzyloxy)phenyl]-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (86 g) as a purple solid.

Workup

  1. stirringthe mixture was stirred for 15 min
  2. stirringthe mixture was stirred for 15 min
  3. stirringthe mixture was stirred for 20 min
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water (1.3 L)
  6. customdried in air
  7. waitblowing for 30 min
  8. washThe precipitate was washed with IPE (1.5 L)
  9. customdried in vacuo at 55° C. for 2.5 h
  10. stirringthe mixture was stirred at room temperature for 1 h
  11. filtrationThe precipitate was collected by filtration
  12. washwashed with IPE (500 mL)
  13. customdried in vacuo

Sources & evidence

ORD record
ord-5d131fe81c9a4acbbdfc48a410c6d5c6
Source dataset
uspto-grants-2014_09
Patent number
US08846713B2

Reaction notes

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