HCID 58181131, compound → 1-{1-[6-(4-Hydroxy-3,5-dimethyl-benzoyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

HRID 469419Notes

Reaction equation

HRID 469419 reaction equation
C([O:8][C:9]1[C:38]([CH3:39])=[CH:37][C:12]([C:13]([C:15]2[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]=2)=[O:14])=[CH:11][C:10]=1[CH3:40])C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:8][C:9]1[C:10]([CH3:40])=[CH:11][C:12]([C:13]([C:15]2[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]=2)=[O:14])=[CH:37][C:38]=1[CH3:39]

Participants

5

Reactant 2

HCID 58181131HCID 58181131, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 581811631-{1-[6-(4-Hydroxy-3,5-dimethyl-benzoyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

50 mg palladium/charcoal (10%) were added to 390 mg (0.7 mmol) 1-{1-[6-(4-benzyloxy-3,5-dimethyl-benzoyl)-pyrimidin-4-yl]-piperidin-4-yl}-1,3-dihydro-imidazo[4,5-b]pyridin-2-one in 50 mL MeOH and the mixture was hydrogenated for 40 min in a 5 psi hydrogen atmosphere at RT. The catalyst was removed by suction filtering and the filtrate was evaporated down. The residue was triturated with some MeOH, suction filtered and washed with diethyl ether. The suction filtered catalyst was decocted with 120 mL MeOH for 1 h, filtered hot and the filtrate was evaporated down. The residue was triturated with a little MeOH, suction filtered and dried. The two batches of solid were combined and purified by preparative HPLC-MS. The fractions containing the product were combined and freeze-dried.

Workup

  1. customThe catalyst was removed by suction
  2. filtrationfiltering
  3. customthe filtrate was evaporated down
  4. customThe residue was triturated with some MeOH, suction
  5. filtrationfiltered
  6. washwashed with diethyl ether
  7. filtrationThe suction filtered catalyst
  8. filtrationfiltered hot
  9. customthe filtrate was evaporated down
  10. customThe residue was triturated with a little MeOH, suction
  11. filtrationfiltered
  12. customdried
  13. custompurified by preparative HPLC-MS
  14. additionThe fractions containing the product
  15. customfreeze-dried

Sources & evidence

ORD record
ord-43cba0e835634ff9a1251a4f86d8cd9a
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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