Water → 6-Chloro-2-methyl-4-(5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)pyridazin-3(2H)-one

HRID 1919125Notes

Reaction equation

HRID 1919125 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)=[CH:14][N:13]=2)[C:6](=[O:10])[N:7]([CH3:9])[N:8]=1.[O:24]1[CH2:27][C:26](=O)[CH2:25]1.[BH3-]C#N.[Na+].O>CO.[Cl-].[Zn+2].[Cl-]>[Cl:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][N:21]([CH:26]4[CH2:27][O:24][CH2:25]4)[CH2:20][CH2:19]3)=[CH:14][N:13]=2)[C:6](=[O:10])[N:7]([CH3:9])[N:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 150242543-OxetanoneHCID 670162986-Chloro-2-methyl-4-(5-(piperazin-1-yl)pyridin-2-ylamino)pyridazin-3(2H)-one Hydrochloride

Product 1

HCID 580440166-Chloro-2-methyl-4-(5-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-2-ylamino)pyridazin-3(2H)-oneYield 50%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 328b (1.2 g, 3.5 mmol), oxetan-3-one (0.5 g, 7.0 mmol), NaBH3CN (0.44 g, 7.0 mmol) and zinc chloride (0.93 g, 7.0 mmol) in methanol (125 ml) was stirred at 50 degree for 3.5 hours. The mixture was added to water and extracted with methylene chloride. The organic layers were combined and concentrated under reduced pressure. The residue was purified by column chromatography eluting with 25:1 methylene chloride/methanol to give 328c (0.63 g, 50%). MS: [M+H]+ 377.

Workup

  1. extractionextracted with methylene chloride
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column chromatography
  4. washeluting with 25:1 methylene chloride/methanol

Sources & evidence

ORD record
ord-0ceb0a88622049e19c13c7e32a101d63
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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