Potassium Carbonate → HCID 86683607, compound

HRID 1509208Notes

Reaction equation

HRID 1509208 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:20][C:21]4[NH:22][S:23](=[O:29])(=[O:28])[CH2:24][O:25][C:26]=4[N:27]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:44][C:45]#[N:46]>CN(C)C=O.C(=O)(O)[O-].[Na+]>[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[C:19]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[CH:20][C:21]4[N:22]([CH2:44][C:45]#[N:46])[S:23](=[O:28])(=[O:29])[CH2:24][O:25][C:26]=4[N:27]=3)=[CH:16][CH:17]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 123139090HCID 123139090, compound

Product 1

HCID 86683607HCID 86683607, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

In a 15 mL reaction tube was added tert-butyl(1-(4-(2,2-dioxido-7-phenyl-1H-pyrido[3,2-e][1,3,4]oxathiazin-6-yl)phenyl)cyclobutyl)carbamate (50 mg, 0.099 mmol), potassium carbonate (41 mg, 0.296 mmol) and 2-bromoacetonitrile (0.021 mL, 0.296 mmol) in anhydrous N,N-dimethylformamide (1 mL) to give a yellow suspension. The reaction mixture was stirred at room temperature for one hour. The reaction mixture was allowed to cool to room temperature, diluted with saturated sodium bicarbonate solution (5 mL) and extracted into dichloromethane (3×3 mL). The combined organic phases were dried over Na2SO4, filtered and concentrated to dryness under reduced pressure to give a yellow oil. This was purified by Biotage chromatography (cyclohexane:ethyl acetate, gradient elution from 90:10 to 20:80) to give the desired product as a colourless oil (32 mg, 59% yield). 1H-NMR (500 MHz, CDCl3) δ 8.04 (1H, s), 7.25-7.38 (7H, m), 7.17-7.25 (2H, m), 5.32 (2H, s), 5.05 (1H, br s), 4.73 (2H, s), 2.20-2.65 (4H, m), 2.00-2.18 (1H, m), 1.77-1.90 (1H, m), 1.05-1.55 (9H, br m). LCMS (Method D) RT=1.60 min, M+H+=547.10.

Workup

  1. customIn a 15 mL reaction tube
  2. customto give a yellow suspension
  3. temperatureto cool to room temperature
  4. extractionextracted into dichloromethane (3×3 mL)
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness under reduced pressure
  8. customto give a yellow oil
  9. customThis was purified by Biotage chromatography (cyclohexane:ethyl acetate, gradient elution from 90:10 to 20:80)

Sources & evidence

ORD record
ord-34aa758d955942979ddb5d6af4d18ae2
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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