HCID 136502896, compound → HCID 178423527, compound

HRID 1775206Notes

Reaction equation

HRID 1775206 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:19](=[O:20])[NH:18][N:17]=[C:7]3[CH2:8][C:9]([CH3:16])([CH3:15])[CH2:10][C:11]4[NH:12][C:13]([CH:14]=1)=[C:5]2[C:6]=43.C(=O)([OH:23])N>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:19](=[O:20])[NH:18][N:17]=[C:7]3[CH2:8][C:9]([CH3:16])([CH3:15])[C:10](=[O:23])[C:11]4[NH:12][C:13]([CH:14]=1)=[C:5]2[C:6]=43

Participants

3

Reactant 1

HCID 136502896HCID 136502896, compound

Product 1

HCID 178423527HCID 178423527, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of carbamate 8-fluoro-2,2-dimethyl-2,3,5,10-tetrahydro-[1,2]diazepino[3,4,5,6-def]carbazol-6(1H)-one (0.5 g, 1.8 mmol) in anhydrous dioxane (25 mL) was added SeO2 (0.32 g, 2.7 mmol). The mixture was refluxed for 40 h and filtered through Celite. The solid material was thoroughly washed with Et2O. The filtrate was concentrated, and the residue was chromatographed to give product (200 mg, 38%) as a solid. 1H NMR (DMSO-d6) δ 12.70 (s, 1H), 10.90 (s, 1H), 7.41 (dd, 1H, J=10.2, 1.8 Hz), 7.09 (dd, 1H, J=9.6, 1.8 Hz), 2.87 (s, 2H), 1.23 (s, 6H). MS (ESI) m/e [M+1]+ 286.

Workup

  1. temperatureThe mixture was refluxed for 40 h
  2. filtrationfiltered through Celite
  3. washThe solid material was thoroughly washed with Et2O
  4. concentrationThe filtrate was concentrated
  5. customthe residue was chromatographed

Sources & evidence

ORD record
ord-b1005aac711c4568ab3033edcfe2ac73
Source dataset
uspto-grants-2016_02
Patent number
US09260440B2

Reaction notes

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