HCID 66794299, compound → 7-(2-Chloro-ethoxy)-2-(4-amino-phenyl)-benzo[d]imidazo[2,1-b]thiazole

HRID 1038325Notes

Reaction equation

HRID 1038325 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:25]=[CH:24][C:8]2[N:9]3[CH:14]=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=4)[N:12]=[C:10]3[S:11][C:7]=2[CH:6]=1.[H][H]>CO.C1COCC1.[Pd]>[Cl:1][CH2:2][CH2:3][O:4][C:5]1[CH:25]=[CH:24][C:8]2[N:9]3[CH:14]=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=4)[N:12]=[C:10]3[S:11][C:7]=2[CH:6]=1

Participants

6

Reactant 2

HCID 66794299HCID 66794299, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 667940197-(2-Chloro-ethoxy)-2-(4-amino-phenyl)-benzo[d]imidazo[2,1-b]thiazole

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-(2-chloro-ethoxy)-2-(4-nitro-phenyl)-benzo[d]imidazo[2,1-b]thiazole (1 equivalent) and 10% Pd/C (0.05-0.1 equivalents) in a mixture of MeOH and THF under 1 atmosphere of hydrogen gas is stirred at rt until the reaction is substantially complete as monitored by LCMS or TLC. The mixture is filtered through Celite and concentrated under reduced pressure. The residue is purified by silica gel flash chromatography to afford 7-(2-chloro-ethoxy)-2-(4-amino-phenyl)-benzo[d]imidazo[2,1-b]thiazole.

Workup

  1. filtrationThe mixture is filtered through Celite
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-d6c2365c23694bef95ba2c7e1a4937ea
Source dataset
uspto-grants-2013_10
Patent number
US08551963B2

Reaction notes

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