Cesium carbonate → HCID 178526676, compound

HRID 707297Notes

Reaction equation

HRID 707297 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@H:11]1[CH2:14][C@H:13]([NH2:15])[CH2:12]1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:23]1[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][CH:26]=[CH:25][N:24]=1>CS(C)=O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@H:11]1[CH2:12][C@H:13]([NH:15][C:23]2[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][CH:26]=[CH:25][N:24]=2)[CH2:14]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 796132-Chloro-3-nitropyridineHCID 178511738HCID 178511738, compound

Product 1

HCID 178526676HCID 178526676, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

The crude amine from step 1, cesium carbonate (2.500 g, 1.535 mmol), 2-chloro-3-nitropyridine (394 mg, 2.488 mmol), and dry dimethylsulfoxide (5 mL) were added and the reaction mixture was stirred at 120° C. for 2 hours. The reaction was cooled and partitioned between water (100 mL), saturated sodium bicarbonate (20 mL) and ethyl acetate. The organic phase was dried with magnesium sulfate and evaporated to dryness under reduced pressure. Purification using silica chromatography (dichloromethane to ethyl acetate gradient) gave the desired trans-N1-(benzo[d]thiazol-2-yl)-N3-(3-nitropyridin-2-yl)cyclobutane-1,3-diamine (580 mg, 1.699 mmol, 75% yield) as light-yellow solid.

Workup

  1. temperatureThe reaction was cooled
  2. custompartitioned between water (100 mL), saturated sodium bicarbonate (20 mL) and ethyl acetate
  3. dry with materialThe organic phase was dried with magnesium sulfate
  4. customevaporated to dryness under reduced pressure
  5. customPurification

Sources & evidence

ORD record
ord-ec35f6ed88dc44c789174b5c48e51f51
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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