Methanol → 1-{1-[6-(4-Amino-2,3-dihydroindole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

HRID 74642Notes

Reaction equation

HRID 74642 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][N:8]2[C:13]([C:15]1[N:20]=[CH:19][N:18]=[C:17]([N:21]2[CH2:26][CH2:25][CH:24]([N:27]3[C:35]4[C:30](=[N:31][CH:32]=[CH:33][CH:34]=4)[NH:29][C:28]3=[O:36])[CH2:23][CH2:22]2)[CH:16]=1)=[O:14])([O-])=O.CO.[H][H]>[Pd].C1COCC1>[NH2:1][C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH2:6][CH2:7][N:8]2[C:13]([C:15]1[N:20]=[CH:19][N:18]=[C:17]([N:21]2[CH2:22][CH2:23][CH:24]([N:27]3[C:35]4[C:30](=[N:31][CH:32]=[CH:33][CH:34]=4)[NH:29][C:28]3=[O:36])[CH2:25][CH2:26]2)[CH:16]=1)=[O:14]

Participants

6

Reactant 3

HCID 887MethanolHCID 583863791-{1-[6-(4-Nitro-2,3-dihydroindole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydroimidazo[4,5-b]pyridin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 583865791-{1-[6-(4-Amino-2,3-dihydroindole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under a hydrogen atmosphere 130 mg (0.27 mmol) 1-{1-[6-(4-nitro-2,3-dihydroindole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydroimidazo[4,5-b]pyridin-2-one and 25 mg palladium on charcoal (10%) were hydrogenated in a 1:1 mixture methanol:THF (15 mL of each) at RT and 3 bar hydrogen pressure. Then the catalyst was eliminated by suction filtering and the residue was washed with 50 mL DMF. The filtrate was evaporated down i. vac., the residue was stirred with methanol and suction filtered. The solid was dried at 50° C. in the CAD.

Workup

  1. customat RT
  2. filtrationfiltering
  3. washthe residue was washed with 50 mL DMF
  4. customThe filtrate was evaporated down i
  5. filtrationfiltered
  6. customThe solid was dried at 50° C. in the CAD

Sources & evidence

ORD record
ord-536eddd31b354d0c8012493596f0ad75
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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