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

HRID 69160Notes

Reaction equation

HRID 69160 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([C:19]2[N:23]3[N:24]=[C:25]([C:28]4[CH:29]=[N:30][N:31]([CH3:33])[CH:32]=4)[CH:26]=[CH:27][C:22]3=[N:21][CH:20]=2)=O)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.C([SiH](CC)CC)C>C(O)C>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][C:19]2[N:23]3[N:24]=[C:25]([C:28]4[CH:29]=[N:30][N:31]([CH3:33])[CH:32]=4)[CH:26]=[CH:27][C:22]3=[N:21][CH:20]=2)=[CH:15][CH:16]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 12052TriethylsilaneHCID 4311764Sodium borohydrideHCID 68633986(4-benzyloxy-phenyl)-[6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanone

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride was added to a solution of (4-benzyloxy-phenyl)-[6-(1-methyl-1H-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanone (Stage 5.2, 190 mg, 0.46 mmol) in ethanol (1.5 mL) and the reaction stirred for 16 h. Water was added to the reaction and the resulting solid was filtered off and dried under vacuum. The solid was dissolved in TFA (2 mL) and to this solution was added triethylsilane (0.18 mL, 1.16 mmol) and the mixture was stirred at rt for 30 min. Water was added and the mixture extracted with EtOAc. The EtOAc extract was dried, filtered and concentrated to give the title compound as red solid (tR 1.3 min (conditions 2), MH+=396).

Workup

  1. filtrationthe resulting solid was filtered off
  2. customdried under vacuum
  3. dissolutionThe solid was dissolved in TFA (2 mL) and to this solution
  4. stirringthe mixture was stirred at rt for 30 min
  5. extractionthe mixture extracted with EtOAc
  6. extractionThe EtOAc extract
  7. customwas dried
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-53679f93851e4b829968e8c918c34ff3
Source dataset
uspto-grants-2014_09
Patent number
US08822468B2

Reaction notes

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