Hydrochloric Acid → 6-[4-(2-Oxo-2,3-dihydroimidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]pyrimidine-4-carboxylic acid

HRID 74506Notes

Reaction equation

HRID 74506 reaction equation
[OH-].[Na+].[O:3]=[C:4]1[NH:12][C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[N:5]1[CH:13]1[CH2:18][CH2:17][N:16]([C:19]2[N:24]=[CH:23][N:22]=[C:21]([C:25]([O:27]CC)=[O:26])[CH:20]=2)[CH2:15][CH2:14]1.O.Cl>C1COCC1>[O:3]=[C:4]1[NH:12][C:7]2=[N:8][CH:9]=[CH:10][CH:11]=[C:6]2[N:5]1[CH:13]1[CH2:14][CH2:15][N:16]([C:19]2[N:24]=[CH:23][N:22]=[C:21]([C:25]([OH:27])=[O:26])[CH:20]=2)[CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 58386714Ethyl 6-[4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]-pyrimidine-4-carboxylate

Product 1

HCID 583866966-[4-(2-Oxo-2,3-dihydroimidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]pyrimidine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

9.0 mL (36.0 mmol) of a 4M NaOH solution were added to 5.50 g (14.9 mmol) ethyl 6-[4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]-pyrimidine-4-carboxylate, 25 mL water in 150 mL THF. After 3 h stirring at RT the THF was eliminated i. vac. The aqueous residue was combined with 9 mL of a 4M hydrochloric acid solution. After 3 h stirring at RT the precipitate was suction filtered and dried in the CAD at 60 C.

Workup

  1. filtrationfiltered
  2. customdried in the CAD at 60 C

Sources & evidence

ORD record
ord-c9c0c15ce1eb4550bb0bf8ff92c33d9a
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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