Potassium Carbonate → HCID 66820027, compound

HRID 473840Notes

Reaction equation

HRID 473840 reaction equation
[NH:1]1[CH2:4][CH:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[NH2:19][C:20]1[C:25]([S:26](Cl)(=[O:28])=[O:27])=[CH:24][C:23]([Br:30])=[CH:22][N:21]=1>O1CCOCC1.O>[NH2:19][C:20]1[C:25]([S:26]([N:1]2[CH2:4][CH:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])[CH2:2]2)(=[O:28])=[O:27])=[CH:24][C:23]([Br:30])=[CH:22][N:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 15194053-Aminoazetidine, 3-BOC protectedHCID 533020262-Amino-5-bromopyridine-3-sulfonyl chloride

Product 1

HCID 66820027HCID 66820027, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl azetidin-3-ylcarbamate (64 mg, 0.37 mmol) and potassium carbonate (102 mg, 0.74 mmol) in dioxane (2 mL) and water (400 uL) was added 2-amino-5-bromopyridine-3-sulfonyl chloride (100 mg, 0.37 mmol, prepared according to the methods in WO2008144463). The reaction mixture was stirred for 1 h at room temperature then quenched by addition of saturated aqueous sodium bicarbonate, and the aqueous solution was extracted twice with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated to provide tert-butyl 1-(2-amino-5-bromopyridin-3-ylsulfonyl)azetidin-3-ylcarbamate (120 mg, 0.30 mmol, 80% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.31 (d, 1H), 8.00 (d, 1H), 5.76 (br s, 2H), 4.80 (br s, 1H), 4.50-4.36 (m, 1H), 4.11 (t, 2H), 3.75 (t, 2H), 1.42 (s, 9H); MS (EI) for C13H19BrN4O4S: 407, 409 (Br isotopes, MH+).

Workup

  1. customprepared
  2. customthen quenched by addition of saturated aqueous sodium bicarbonate
  3. extractionthe aqueous solution was extracted twice with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6eb0583a80514da3b62028ec623efb4a
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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