Methanol → HCID 59680103, compound

HRID 419875Notes

Reaction equation

HRID 419875 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[N:16]=[C:17]3[N:21]([CH:22]=2)[C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[N+:29]([O-])=O)=[CH:19][S:18]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.O.[SH-].[Na+]>O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][C:15]2[N:16]=[C:17]3[N:21]([CH:22]=2)[C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[NH2:29])=[CH:19][S:18]3)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 16211346Sodium hydrosulfide hydrateHCID 59680214HCID 59680214, compound

Product 1

HCID 59680103HCID 59680103, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-[3-(2-Nitro-phenyl)-imidazo[2,1-b]thiazol-6-ylmethyl]-piperazine-1-carboxylic acid tert-butyl ester (320 mg, 0.73. mmol) was mixed with 20 mL of MeOH and 5 mL of water containing sodium hydrosulfide hydrate (244 mg, 6 eq). The reaction mixture was stirred under reflux for 4 hours. It was then cooled to room temperature and concentrated. The aqueous layer was extracted with CH2Cl2. The combined organic layers were dried (Na2SO4) and concentrated to afford 280 mg of 4-[3-(2-amino-phenyl)-imidazo[2,1-b]thiazol-6-ylmethyl]-piperazine-1-carboxylic acid tert-butyl ester (92% yield).

Workup

  1. temperatureunder reflux for 4 hours
  2. concentrationconcentrated
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-876cbdfff3584361a3b07fb07834219c
Source dataset
uspto-grants-2012_01
Patent number
US08093401B2

Reaction notes

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