Potassium Carbonate → HCID 123759853, compound

HRID 1509239Notes

Reaction equation

HRID 1509239 reaction equation
[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:20][C:21]4[NH:26][C:25](=[O:27])[CH:24]([CH2:28][O:29][CH3:30])[O:23][C:22]=4[N:31]=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[CH2:46][C:47]#[N:48]>CN(C=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:38])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[CH:20][C:21]4[N:26]([CH2:46][C:47]#[N:48])[C:25](=[O:27])[CH:24]([CH2:28][O:29][CH3:30])[O:23][C:22]=4[N:31]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 123924337HCID 123924337, compound

Product 1

HCID 123759853HCID 123759853, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl(1-(4-(3-(methoxymethyl)-2-oxo-7-phenyl-2,3-dihydro-1H-pyrido[2,3-b][1,4]oxazin-6-yl)phenyl)cyclobutyl)carbamate (60 mg, 0.116 mmol) in DMF (2 ml) was added potassium carbonate (48 mg) and 2-bromoacetonitrile (41.9 mg, 0.349 mmol). The reaction mixture was stirred at room temperature for 16 h then was diluted with ethyl acetate (20 ml). Washed with water, brine, and dried with Na2SO4, filtered and concentrated to give crude product which was purified by column (biotage, 25 g) eluted with ethyl acetate and cyclohexane to afford product (35 mg). 1H NMR (500 MHz, CDCl3): 7.20-7.33 (m, 10H), 5.10 (t, 1H), 4.97 (s, 1H), 4.82 (dd, 2H), 4.03 (dd, 2H), 3.36 (s, 3H), 2.44-2.50 (m, 4H), 2.06 (m, 1H), 1.80 (m, 1H), 1.24-1.36 (br, 9H).

Workup

  1. washWashed with water, brine
  2. dry with materialdried with Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give crude product which
  6. customwas purified by column (biotage, 25 g)
  7. washeluted with ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-3f613f8fcc694481b5fb3d1b99fb2970
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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