HCID 23135143, compound → HCID 178458131, compound

HRID 475510Notes

Reaction equation

HRID 475510 reaction equation
C([N:8]1[C:12]2[CH2:13][CH:14]([O:16][CH2:17][CH2:18][CH3:19])[CH2:15][C:11]=2[C:10]([C:20]2[N:21]=[N:22][NH:23][N:24]=2)=[N:9]1)C1C=CC=CC=1.CC(C)([O-])C.[K+]>CS(C)=O>[CH2:17]([O:16][CH:14]1[CH2:15][C:11]2=[C:10]([C:20]3[NH:24][N:23]=[N:22][N:21]=3)[NH:9][N:8]=[C:12]2[CH2:13]1)[CH2:18][CH3:19]

Participants

4

Reactant 2

HCID 23135143HCID 23135143, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 178458131HCID 178458131, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of the intermediate from step B (26 mg, 0.08 mmol) in DMSO (0.6 mL) was added potassium-t-butoxide (0.6 mL, 0.6 mmol, 1.0 M in THF). Oxygen gas was bubbled through the reaction mixture for 15 minutes. The reaction was quenched with HCl (3 mL, 3N). The resulting mixture was extracted with ethyl acetate (5×) dried over anhydrous Na2SO4 filtered and concentrated in vacuo. The residue was purified by reverse phase HPLC to afford the title compound. 1H NMR (CDCl3) δ 4.80 (m, 1H), 3.51 (m, 2H), 3.24 (dd, J=6.8, 15.5 Hz, 1H), 3.18 (dd, J=6.9, 16.0 Hz, 1H), 2.85 (dd, J=4.1, 15.6 Hz, 1H), 2.79 (dd, J=4.4, 16.1 Hz, 1H), 1.62 (m, 2H), 0.96 (t, J=7.6 Hz, 3H). LC-MS: 2.15 min; (M+H)=235.

Workup

  1. customOxygen gas was bubbled through the reaction mixture for 15 minutes
  2. customThe reaction was quenched with HCl (3 mL, 3N)
  3. extractionThe resulting mixture was extracted with ethyl acetate (5×)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-b041a70ca341465c8ea498249d7a080c
Source dataset
uspto-grants-2014_01
Patent number
US08637555B2

Reaction notes

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