Water → Ethyl 6-[4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]-pyrimidine-4-carboxylate

HRID 74505Notes

Reaction equation

HRID 74505 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([N:9]2[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]2=[O:18])[CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.Cl[C:29]1[N:34]=[CH:33][N:32]=[C:31]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:30]=1.O>CN(C=O)C.C(OCC)(=O)C>[O:18]=[C:10]1[NH:11][C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:17]2[N:9]1[CH:6]1[CH2:5][CH2:4][N:3]([C:29]2[N:34]=[CH:33][N:32]=[C:31]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH:30]=2)[CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 222931811-(piperidin-4-yl)-1H,2H,3H-imidazo[4,5-b]pyridin-2-one dihydrochlorideHCID 22756838Ethyl 6-chloropyrimidine-4-carboxylate

Product 1

HCID 58386714Ethyl 6-[4-(2-oxo-2,3-dihydro-imidazo[4,5-b]pyridin-1-yl)-piperidin-1-yl]-pyrimidine-4-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5.40 g (18.6 mmol) 1-piperidin-4-yl-1,3-dihydro-imidazo[4,5-b]pyridin-2-one dihydrochloride and 11 mL (63.93 mmol) DIPEA were added to 3.40 g (18.2 mmol) ethyl 6-chloropyrimidine-4-carboxylate in 80 mL DMF. After 3 h stirring at RT the solvent was eliminated i.vac. The residue was combined with 70 mL water and stirred for 10 min. 5 mL ethyl acetate were added and the mixture was stirred vigorously. The precipitated solid was suction filtered and dried at 40° C. in the circulating air dryer.

Workup

  1. stirringstirred for 10 min
  2. stirringthe mixture was stirred vigorously
  3. filtrationfiltered
  4. customdried at 40° C. in the circulating air dryer

Sources & evidence

ORD record
ord-09d2239937e34d2fa4085787b66d3521
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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