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

HRID 926017Notes

Reaction equation

HRID 926017 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

7-(2-Morpholin-4-yl-ethoxy)-2-(4-nitrophenyl)imidazo[2,1-b]benzothiazole was dissolved into methanol and THF and placed in a hydrogenator. Raney nickel was added and the vessel was pressurized with hydrogen and stirred for >24 hours. The reaction mixture was concentrated to a thick paste and diluted with methyl tert-butyl ether. The resulting solids were filtered and washed with methyl tert-butyl ether and dried under vacuum to give 7-(2-morpholin-4-yl-ethoxy)-2-(4-aminophenyl) imidazo[2,1-b]benzothiazole.

Workup

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

Sources & evidence

ORD record
ord-8b091454dc62435ab6a85882e079e84f
Source dataset
uspto-grants-2016_03
Patent number
US09284332B2

Reaction notes

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