tert-Butyl (2-chloroacetyl)carbamate → [6-(6-Bromo-benzotriazol-1-ylmethyl)-imidazo[1,2-b]pyridazin-2-yl]-carbamic acid tert-butyl ester

HRID 1925116Notes

Reaction equation

HRID 1925116 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[N:8][N:7]([CH2:10][C:11]3[N:16]=[N:15][C:14]([NH2:17])=[CH:13][CH:12]=3)[C:6]=2[CH:18]=1.[C:19]([O:23][C:24](=[O:30])[NH:25][C:26](=O)[CH2:27]Cl)([CH3:22])([CH3:21])[CH3:20]>CC(N(C)C)=O>[C:19]([O:23][C:24](=[O:30])[NH:25][C:26]1[N:17]=[C:14]2[CH:13]=[CH:12][C:11]([CH2:10][N:7]3[C:6]4[CH:18]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=4[N:9]=[N:8]3)=[N:16][N:15]2[CH:27]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 14221822tert-Butyl (2-chloroacetyl)carbamateHCID 592330216-(6-Bromo-benzotriazol-1-ylmethyl)-pyridazin-3-ylamine

Product 1

HCID 59233266[6-(6-Bromo-benzotriazol-1-ylmethyl)-imidazo[1,2-b]pyridazin-2-yl]-carbamic acid tert-butyl esterYield 30.9%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of compound 10G (1.0 g, 3.28 mmol), (2-chloro-acetyl)-carbamic acid tert-butyl ester (1.0 g, 5.0 mmol) and Na2HPO4 (1.4 g, 10 mmol) in DMA (50 mL) was stirred at 135° C. for four hours. Solvent was removed under reduced pressure. The residue was sonicated in ethyl acetate/water, and the precipitate was filtered off. Ethyl acetate solution was separated and concentrated and loaded on silica gel. The silica column was eluted with hexane/ethyl acetate (1/2) to give 0.45 g of desired product (10H). ESI-MS:m/z 444.1 (M+H)+.

Workup

  1. customSolvent was removed under reduced pressure
  2. customThe residue was sonicated in ethyl acetate/water
  3. filtrationthe precipitate was filtered off
  4. customEthyl acetate solution was separated
  5. concentrationconcentrated
  6. washThe silica column was eluted with hexane/ethyl acetate (1/2)

Sources & evidence

ORD record
ord-7c1bea8a86044366bbbbc54856e4bb81
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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