Bcl-2 Inhibitor → HCID 11076565, compound

HRID 899170Notes

Reaction equation

HRID 899170 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]2[N+:7]([O-])=[N+:8]([O-])[C:9]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:10]=3[CH2:11][CH2:12][C:5]=2[CH:4]=1.COC1C=CC(N=O)=C(CCC2C=C(OC)C=CC=2N=O)C=1>>[CH3:18][O:17][C:14]1[CH:15]=[CH:16][C:9]([NH2:8])=[C:10]([CH2:11][CH2:12][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:22]=[CH:21][C:6]=2[NH2:7])[CH:13]=1

Participants

3

Reactant 2

HCID 11822705Bcl-2 InhibitorHCID 178487117HCID 178487117, compound

Product 1

HCID 11076565HCID 11076565, compound

Procedure

A solution of compound 42 (2.46 g, 9.04 mmol) and sodium tunsgtate dihydrate (0.42 g, 1.26 mmol) in 95% ethanol (27.13 ml) and water (9.04 ml) was cooled to 5° C. and treated dropwise with 30% H2O2 (4.61 ml). The reaction mixture was stirred for 5 h at 5° C., then 10 ml of a saturated aqueous solution of NH4Cl was added, and extracted with CH2Cl2 (3×30 ml). The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure to afford the crude product. Recrystallization in CH2Cl2/hexanes afforded 1.22 g (4.06 mmol, 45%) of green crystals. The mother solution was concentrated under reduced pressure, and the residue purified by flash chromatography on silica gel with hexanes/ethyl acetate: 3/1 as eluant to give an additional 0.431 g (1.47 mmol, 16%) of compounds 6a and 6b as green crystals. mp: 136-138° C.

Workup

  1. concentrationThe mother solution was concentrated under reduced pressure
  2. customthe residue purified by flash chromatography on silica gel with hexanes/ethyl acetate

Sources & evidence

ORD record
ord-c2c37f5936924c9bb8822702990fa3fa
Source dataset
uspto-grants-2008_04
Patent number
US07354928B2

Reaction notes

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