Methanol → HCID 58386388, compound

HRID 74643Notes

Reaction equation

HRID 74643 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]([C:15]1[N:20]=[CH:19][N:18]=[C:17]([N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[C:35]5[C:30](=[N:31][CH:32]=[CH:33][CH:34]=5)[NH:29][C:28]4=[O:36])[CH2:23][CH2:22]3)[CH:16]=1)=[O:14])[CH2:8][CH2:7]2)([O-])=O.CO.[H][H]>[Pd].C1COCC1>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]([C:15]1[N:20]=[CH:19][N:18]=[C:17]([N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[C:35]5[C:30](=[N:31][CH:32]=[CH:33][CH:34]=5)[NH:29][C:28]4=[O:36])[CH2:23][CH2:22]3)[CH:16]=1)=[O:14])[CH2:8][CH2:7]2

Participants

6

Reactant 3

HCID 887MethanolHCID 583865751-{1-[6-(5-Nitro-2,3-dihydro-indole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 58386388HCID 58386388, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under a hydrogen atmosphere 30 mg (0.06 mmol) 1-{1-[6-(5-nitro-2,3-dihydro-indole-1-carbonyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one and 10 mg palladium on charcoal (10%) were hydrogenated in a 1:1 mixture methanol:THF (5 mL each) at RT and 3 bar hydrogen pressure. Then the catalyst was removed by suction filtering and the filtrate was evaporated down i. vac. The residue was dissolved in 1 mL DMF, filtered through a syringe filter and purified by preparative HPLC. The product fractions were combined and lyophilised.

Workup

  1. customat RT
  2. customThen the catalyst was removed by suction
  3. filtrationfiltering
  4. customthe filtrate was evaporated down i
  5. dissolutionThe residue was dissolved in 1 mL DMF
  6. filtrationfiltered through a syringe
  7. filtrationfilter
  8. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-0f48689e6d154e14b67a934278e29e23
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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