Sodium cyanoborohydride → HCID 86684122, compound

HRID 1024014Notes

Reaction equation

HRID 1024014 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([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:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[O:24]1[CH2:27][C:26](=O)[CH2:25]1.[BH3-]C#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-].CCOCC>[Cl:1][C:2]1[CH:3]=[C:4]([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:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1

Participants

6

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 150242543-OxetanoneHCID 866841216-Chloro-N-(5-(piperazin-1-yl)pyridine-2-yl)imidazo[1,2-a]pyridin-8-amine

Product 1

HCID 86684122HCID 86684122, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 162251561ZINC;ethoxyethane;dichlorideCatalystHCID 887MethanolSolvent

Procedure

A mixture of 102b (0.773 g, 1.75 mmol), oxetan-3-one (0.189 g, 2.62 mmol), NaBH3CN (0.22 g, 3.5 mmol), and zinc chloride/Et2O (3.5 ml, 3.5 mmol) in methanol (40 mL) was stirred at 50˜60° C. for 5 hours. The solid was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography eluting with 5:1 CH2Cl2/methanol to afford 102c (200 mg, 30%). MS: [M+H]+ 385.

Workup

  1. customThe solid was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by column chromatography
  4. washeluting with 5:1 CH2Cl2/methanol

Sources & evidence

ORD record
ord-ec592ed5d04c4bfc95378f21248e8c6b
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

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