Ammonium formate → HCID 67466955, compound

HRID 2284373Notes

Reaction equation

HRID 2284373 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[N:13][CH:12]=2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.C([O-])=O.[NH4+]>[OH-].[OH-].[Pd+2].CCO>[N:10]1[CH:9]=[CH:8][N:6]2[C:5]=1[C:4]([C:11]1[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[N:13][CH:12]=1)=[CH:3][CH:2]=[N:7]2

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 86676945HCID 86676945, compound2×

Product 1

HCID 67466955HCID 67466955, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 702EthanolSolvent2×

Procedure

A pressure bottle charged with a mixture of 4-(6-chloroimidazo[1,2-b]pyridazin-8-yl)isoquinoline (270 mg, 0.962 mmol), ammonium formate (243 mg, 3.85 mmol), palladium hydroxide on carbon (67 mg, 0.1 mmol) (20% wet), and EtOH (5 ml). The pressure bottle charged with a mixture of 4-(6-chloroimidazo[1,2-b]pyridazin-8-yl)isoquinoline (270 mg, 0.962 mmol), ammonium formate (243 mg, 3.85 mmol), palladium hydroxide on carbon (67 mg, 0.1 mmol) (20% wet), and EtOH (5 ml) was stirred at room temperature for 5 min. under nitrogen. The resulting mixture was heated to 50° C. for 20 min and cooled to room temperature. The reaction mixture was passed through a pad of CELITE® and washed with MeOH. The filtrate was concentrated and the residue was purified by BIOTAGE® (20-60% EtOAc/CH2Cl2, 1.5 L) to give the product (220 mg, 93%). LC/MS: Rt=0.54 min. LC/MS (Condition A): 247.17.

Workup

  1. temperatureThe resulting mixture was heated to 50° C. for 20 min
  2. temperaturecooled to room temperature
  3. washwashed with MeOH
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by BIOTAGE® (20-60% EtOAc/CH2Cl2, 1.5 L)

Sources & evidence

ORD record
ord-8e86a641227c4af4bcca926439513004
Source dataset
uspto-grants-2015_09
Patent number
US09145419B2

Reaction notes

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