HCID 57929903, compound → HCID 57929880, compound

HRID 1930053Notes

Reaction equation

HRID 1930053 reaction equation
[N:1]([CH2:4][CH2:5][N:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=2[F:18])=[C:9]([C:19]2[CH:20]=[CH:21][C:22]3[N:23]([C:25]([CH:28]([CH3:30])[CH3:29])=[N:26][N:27]=3)[N:24]=2)[CH:8]=[N:7]1)=[N+]=[N-]>CCO.[Pt](=O)=O>[F:18][C:12]1[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:11]=1[C:10]1[N:6]([CH2:5][CH2:4][NH2:1])[N:7]=[CH:8][C:9]=1[C:19]1[CH:20]=[CH:21][C:22]2[N:23]([C:25]([CH:28]([CH3:30])[CH3:29])=[N:26][N:27]=2)[N:24]=1

Participants

4

Reactant 1

HCID 57929903HCID 57929903, compound

Product 1

HCID 57929880HCID 57929880, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

The 6-(1-(2-azidoethyl)-5-(2,4-difluorophenyl)-1H-pyrazol-4-yl)-3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazine (0.485 g, 1.19 mmol; prepared using General Procedure L.1 from 1-(2,4-difluorophenyl)-2-(3-isopropyl-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (Preparation #K.1) with hydroxylethylhydrazine, General Procedure W with methanesulfonyl chloride, General Procedure X.1 with sodium azide) was dissolved in EtOH (20 mL) then platinum (IV) oxide (0.090 g, 0.40 mmol) was added. The mixture was hydrogenated at atmospheric pressure and ambient temperature for about 16 h then filtered through a pad of Celite®. The filtrate was concentrated under reduced pressure to give the title compound (0.447 g, 98%): LC/MS (Table 1, Method a) Rt=1.66 min; MS m/z: 384.3 (M+H)+.

Workup

  1. filtrationthen filtered through a pad of Celite®
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d49c785eb2ec44c4808e3235e084eb87
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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