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

HRID 2250378Notes

Reaction equation

HRID 2250378 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-339f87c1bdf940ffa8e3055e61e08a60
Source dataset
uspto-grants-2008_01
Patent number
US07317021B2

Reaction notes

Loading…