6-{2-[6-(3-Benzyloxy-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-4-methyl-pyridin-2-ylamine → HCID 178428709, compound

HRID 505411Notes

Reaction equation

HRID 505411 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[C:17]3[N:23]=[C:22]([CH2:24][CH2:25][C:26]4[N:31]=[C:30]([NH2:32])[CH:29]=[C:28]([CH3:33])[CH:27]=4)[NH:21][C:18]3=[N:19][CH:20]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[NH2:32][C:30]1[N:31]=[C:26]([CH2:25][CH2:24][C:22]2[NH:21][C:18]3=[N:19][CH:20]=[C:15]([C:11]4[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][CH:12]=4)[CH:16]=[C:17]3[N:23]=2)[CH:27]=[C:28]([CH3:33])[CH:29]=1

Participants

4

Reactant 1

HCID 1784287106-{2-[6-(3-Benzyloxy-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-4-methyl-pyridin-2-ylamine2×

Product 1

HCID 178428709HCID 178428709, compoundYield 22.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

110 mg of 6-{2-[6-(3-benzyloxy-phenyl)-3H-imidazo[4,5-b]pyridin-2-yl]-ethyl}-4-methyl-pyridin-2-ylamine (compound 13) and 33 mg palladium on active carbon (10% Pd) are suspended in 12 ml of methanol. The suspension is vigorously stirred at r.t. for 64 h under a hydrogen atmosphere. The suspension is passed through kieselguhr and rinsed with methanol. The filtrate is concentrated to dryness to afford 53 mg of crude product. Purification by HPLC yields 20 mg of the title compound as a colorless solid. M.p. 162° C. ESI-MS: 346.2 (MH+). TLC: Rf=0.17 (dichloromethane/methanol 10:1).

Workup

  1. washrinsed with methanol
  2. concentrationThe filtrate is concentrated to dryness
  3. customto afford 53 mg of crude product
  4. customPurification by HPLC

Sources & evidence

ORD record
ord-b23e97818e104e2682850a266415f2c7
Source dataset
uspto-grants-2010_08
Patent number
US07781453B2

Reaction notes

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