Methanol → 2-(4-Aminophenyl)-7-(2-morpholin-4-yl-ethoxy)imidazo[2,1-b]-[1,3]benzothiazole

HRID 333719Notes

Reaction equation

HRID 333719 reaction equation
[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:30]=[CH:29][C:13]3[N:14]4[CH:19]=[C:18]([C:20]5[CH:25]=[CH:24][C:23]([N+:26]([O-])=O)=[CH:22][CH:21]=5)[N:17]=[C:15]4[S:16][C:12]=3[CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CO.[H][H]>[Ni].C1COCC1>[N:1]1([CH2:7][CH2:8][O:9][C:10]2[CH:30]=[CH:29][C:13]3[N:14]4[CH:19]=[C:18]([C:20]5[CH:21]=[CH:22][C:23]([NH2:26])=[CH:24][CH:25]=5)[N:17]=[C:15]4[S:16][C:12]=3[CH:11]=2)[CH2:2][CH2:3][O:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 887MethanolHCID 445987167-[2-(4-Morpholinyl)ethoxy]-2-(4-nitrophenyl)imidazo[2,1-b]benzothiazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 445986692-(4-Aminophenyl)-7-(2-morpholin-4-yl-ethoxy)imidazo[2,1-b]-[1,3]benzothiazole

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Intermediate 3 is dissolved into Methanol and THF and placed in a Hydrogenator. Raney Nickel is added and the vessel is pressurized with Hydrogen and stirred for >24 hrs. The reaction mixture is concentrated to a thick paste and diluted with Methyl tert-butyl ether. The resulting solids are filtered and washed with Methyl tert-butyl ether and dried under vacuum to give Intermediate 4.

Workup

  1. concentrationThe reaction mixture is concentrated to a thick paste
  2. additiondiluted with Methyl tert-butyl ether
  3. filtrationThe resulting solids are filtered
  4. washwashed with Methyl tert-butyl ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-7d04506a4eca445d968eab0acfc761e4
Source dataset
uspto-grants-2014_11
Patent number
US08883783B2

Reaction notes

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