3-(4-benzyloxy-benzyl)-6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine → HCID 44206066, compound

HRID 69159Notes

Reaction equation

HRID 69159 reaction equation
C([O:8][C:9]1[CH:30]=[CH:29][C:12]([CH2:13][C:14]2[N:18]3[N:19]=[C:20]([C:23]4[CH:24]=[N:25][N:26]([CH3:28])[CH:27]=4)[CH:21]=[CH:22][C:17]3=[N:16][CH:15]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C(O)C>[CH3:28][N:26]1[CH:27]=[C:23]([C:20]2[CH:21]=[CH:22][C:17]3[N:18]([C:14]([CH2:13][C:12]4[CH:11]=[CH:10][C:9]([OH:8])=[CH:30][CH:29]=4)=[CH:15][N:16]=3)[N:19]=2)[CH:24]=[N:25]1

Participants

4

Reactant 1

HCID 686333193-(4-benzyloxy-benzyl)-6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine

Product 1

HCID 44206066HCID 44206066, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on carbon (49 mg) was added to a solution of 3-(4-benzyloxy-benzyl)-6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazine (Stage 5.1, 214 mg, 0.46 mmol) in ethanol and the resulting mixture was stirred under an atmosphere of hydrogen at rt for 24 h. The RM was filtered through Celite and concentrated in vacuo. Purification by HPLC afforded the title compound as a white solid (tR 0.8 min (conditions 2), MH+=306, 1H-NMR in CD3OD: 8.4 (s, 1H), 8.2 (d, 1H), 8.1 (s, 1H), 8.0 (d, 1H), 7.7 (s, 1H), 7.2 (d, 2H), 6.8 (d, 2H), 4.3 (s, 2H), 4.0 (s, 3H)).

Workup

  1. filtrationThe RM was filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customPurification by HPLC

Sources & evidence

ORD record
ord-f3b8706cfaca4f5591e80e5db4cc0333
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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