Water → (6S)-9-fluoro-4,13-dioxa-2,11,17,21,22,25-hexazapentacyclo[17.5.2.02,6.07,12.022,26]hexacosa-1(25),7(12),8,10,19(26),20,23-heptaene-3,18-dione

HRID 1426962Notes

Reaction equation

HRID 1426962 reaction equation
Cl[CH2:2][CH2:3][CH2:4][NH:5][C:6]([C:8]1[CH:9]=[N:10][N:11]2[CH:16]=[CH:15][C:14]([N:17]3[C@@H:21]([C:22]4[C:23](=[O:29])[NH:24][CH:25]=[C:26]([F:28])[CH:27]=4)[CH2:20][O:19][C:18]3=[O:30])=[N:13][C:12]=12)=[O:7].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[F:28][C:26]1[CH:25]=[N:24][C:23]2[O:29][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:7])[C:8]3=[C:12]4[N:13]=[C:14]([CH:15]=[CH:16][N:11]4[N:10]=[CH:9]3)[N:17]3[C@H:21]([CH2:20][O:19][C:18]3=[O:30])[C:22]=2[CH:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10796Cesium carbonateHCID 86691746(S)-N-(3-chloropropyl)-5-(4-(5-fluoro-2-oxo-1,2-dihydropyridin-3-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Product 1

HCID 54670445(6S)-9-fluoro-4,13-dioxa-2,11,17,21,22,25-hexazapentacyclo[17.5.2.02,6.07,12.022,26]hexacosa-1(25),7(12),8,10,19(26),20,23-heptaene-3,18-dioneYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of (S)-N-(3-chloropropyl)-5-(4-(5-fluoro-2-oxo-1,2-dihydropyridin-3-yl)-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (35 mg, 0.08 mmol) in DMF (3 mL) was added cesium carbonate (79 mg, 0.24 mmol). The mixture was stirred at 65° C. for 30 minutes then at ambient temperature for 48 hours. The mixture was treated with water (30 mL) and extracted with EtOAc (3×10 mL). The combined organic phases were washed with water (5×10 mL) and brine (10 mL), then dried over Na2SO4, filtered and concentrated. The residue was purified via flash column chromatography eluting with 2% MeOH/DCM to afford the title compound (13 mg, 41% yield) as an amorphous white solid. MS (apci) m/z=399.2 (M+H).

Workup

  1. waitat ambient temperature for 48 hours
  2. extractionextracted with EtOAc (3×10 mL)
  3. washThe combined organic phases were washed with water (5×10 mL) and brine (10 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via flash column chromatography
  8. washeluting with 2% MeOH/DCM

Sources & evidence

ORD record
ord-cfd654408cc041598264e5e7afd75756
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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