Trifluoroacetic acid → 5-Dimethylamino-1-methyl-3-piperidin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-one

HRID 967417Notes

Reaction equation

HRID 967417 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:18]3=[N:19][C:20]([N:23]([CH3:25])[CH3:24])=[CH:21][CH:22]=[C:17]3[N:16]([CH3:26])[C:15]2=[O:27])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:24][N:23]([CH3:25])[C:20]1[N:19]=[C:18]2[N:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[C:15](=[O:27])[N:16]([CH3:26])[C:17]2=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 691585984-(5-Dimethylamino-1-methyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 222938675-Dimethylamino-1-methyl-3-piperidin-4-yl-1,3-dihydroimidazo[4,5-b]pyridin-2-oneYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 1.07 g (0.0028 mol) of 4-(5-dimethylamino-1-methyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl)-piperidine-1-carboxylic acid tert-butyl ester in CH2Cl2 (7 mL) was added 7 mL of TFA. After 35 min, the solvent was removed. The residue was partitioned between EtOAc (200 mL) and 1 N NaOH (150 mL). The aqueous layer was extracted with EtOAc (3×100 mL) and the combined organic layers were dried over Na2SO4 and concentrated to afford 0.74 g (96%) of 5-dimethylamino-1-methyl-3-piperidin-4-yl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one as a white/pink solid. 1H NMR (400 MHz, CDCl3): 6.95 (d, J=8.3 Hz, 1H), 6.08 (d, J=8.3 Hz, 1H), 4.35 (tt, J=12.1 Hz, 4.0 Hz, 1H), 3.25 (s, 3H), 3.14 (d, J=12.4 Hz, 2H) 2.97 (s, 6H), 2.66 (td, J=12.9 Hz, 1.3 Hz, 2H), 2.53 (qd, J=12.4 Hz, 4.0 Hz, 2H), 1.69 (d, J=11.9 Hz, 2H).

Workup

  1. customthe solvent was removed
  2. customThe residue was partitioned between EtOAc (200 mL) and 1 N NaOH (150 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (3×100 mL)
  4. dry with materialthe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-03842ca3bc8e4b32aec1cc4fa6dbc9ab
Source dataset
uspto-grants-2005_10
Patent number
US06953793B2

Reaction notes

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