Sodium hydride → HCID 86696419, compound

HRID 870716Notes

Reaction equation

HRID 870716 reaction equation
[Br:1][C:2]1[N:6]2[N:7]=[C:8]([NH:11][CH2:12][CH2:13][OH:14])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[C:15]([N:19]([CH3:28])[C:20](N1C=C[N+](C)=C1)=[O:21])([CH3:18])([CH3:17])[CH3:16].[H-].[Na+]>C1COCC1.CN(C=O)C>[C:15]([N:19]([CH3:28])[C:20](=[O:21])[O:14][CH2:13][CH2:12][NH:11][C:8]1[CH:9]=[CH:10][C:5]2[N:6]([C:2]([Br:1])=[CH:3][N:4]=2)[N:7]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 57418689HCID 57418689, compoundHCID 86589187HCID 86589187, compound

Product 1

HCID 86696419HCID 86696419, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

To a solution of 2-((3-bromoimidazo[1,2-b]pyridazin-6-yl)amino)ethanol (0.35 g, 1.5 mmol) and 1-(tert-butyl(methyl)carbamoyl)-3-methyl-1H-imidazol-3-ium (0.30 g, 1.5 mmol) in THF/DMF (6.0 mL/3.0 mL) was added NaH (0.15 g, 60% in mineral oil, 2.5 mmol). The reaction was stirred for 24 h and then quenched with water, extracted with ether, concentrated and purified by ISCO column chromatography give 2-((3-bromoimidazo[1,2-b]pyridazin-6-yl)amino)ethyl tert-butyl(methyl)carbamate as product (0.17 g, 31% yield). LRMS (ESI) m/e 372.0 [(M+H)+, calcd for C14H21BrN5O2 371.2].

Workup

  1. customquenched with water
  2. extractionextracted with ether
  3. concentrationconcentrated
  4. custompurified by ISCO column chromatography

Sources & evidence

ORD record
ord-47120bc918fd4f65b1e7558a2957636f
Source dataset
uspto-grants-2015_03
Patent number
US08969565B2

Reaction notes

Loading…