Hydrochloric Acid → HCID 86345856, compound

HRID 1772697Notes

Reaction equation

HRID 1772697 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:21]=[C:22]([CH2:24][O:25][C:26]4[CH:35]=[CH:34][C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]=4)[N:23]=3)[C:10]([C:13]3[CH:14]=[CH:15][C:16]([C:19]#[N:20])=[N:17][CH:18]=3)=[CH:11][N:12]=2)[CH2:3][CH2:2]1.[OH-:36].[Na+].OO.Cl>CCO.CS(C)=O>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([CH:21]=[C:22]([CH2:24][O:25][C:26]4[CH:35]=[CH:34][C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]=4)[N:23]=3)[C:10]([C:13]3[CH:14]=[CH:15][C:16]([C:19]([NH2:20])=[O:36])=[N:17][CH:18]=3)=[CH:11][N:12]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 117728040HCID 117728040, compound

Product 1

HCID 86345856HCID 86345856, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of compound 54a (60 mg, 0.13 mmol) in EtOH (4 mL) and DMSO (1 mL) was added a 3N aqueous NaOH (0.06 mL, 0.18 mmol) and 30% hydrogen peroxide (0.3 mL). The reaction mixture was refluxed at 60° C. for 12 h. The reaction mixture was allowed to cool to rt and acidified with 2N HCl to pH˜2 and extracted with DCM (2×30 mL). The combined DCM layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue obtained was purified by flash column chromatography on silica gel (0-10% MeOH/DCM) to give the title compound 84. 1H-NMR (400 MHz, MeOH) δ (ppm): 3.83-3.87 (m, 4H), 4.27-4.32 (m, 4H), 5.62 (s, 2H), 6.90 (d, J=8.8 Hz, 1H), 7.32-7.38 (m, 2H), 7.59 (ddd, J=8.4, 7.0, 1.5 Hz, 1H), 7.65-7.72 (m, 1H), 7.74-7.81 (m, 2H), 7.97 (d, J=8.8 Hz, 1H), 8.03 (dd, J=8.1, 2.2 Hz, 1H), 8.25 (d, J=8.1 Hz, 1H), 8.73 (d, J=1.5 Hz, 1H). (LCMS, ESI pos.) Calcd. for C26H23N7O3: 482.2 [M+H]. found 482.2.

Workup

  1. temperatureto cool to rt
  2. extractionextracted with DCM (2×30 mL)
  3. dry with materialThe combined DCM layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified by flash column chromatography on silica gel (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-44ccbcadbb2c4edc90c41e382e772b04
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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