HCID 68819643, compound → HCID 86045712, compound

HRID 508617Notes

Reaction equation

HRID 508617 reaction equation
[OH:1][CH2:2][C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:5]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([NH2:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[N:4]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH:2]([C:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[N:5]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([NH2:24])(=[O:22])=[O:23])=[CH:17][CH:16]=2)[N:4]=1)=[O:1]

Participants

4

Reactant 2

HCID 68819643HCID 68819643, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 86045712HCID 86045712, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of alcohol 8c (0.46 g, 1.34 mmol) and 0.43 g of powdered 4 Å molecular sieves in 20 mL of DCM, was added PCC (0.43 g, 2.0 mmol) at room temperature. After 6 hours, the reaction mixture was filtered through a 0.75-in. pad of Celite. The filtrate was concentrated in vacuo then the residue was purified by column chromatography to afford the titled compound (0.21 g, 46%) as a white solid. mp 195.9-197.9° C. 1H NMR (300 MHz, DMSO-d6): δ 10.01 (s, 1H), 7.88 (d, J=9 Hz, 2H), 7.56 (d, J=9 Hz, 2H), 7.55-7.52 (m, 2H), 7.25-7.17 (m, 4H), 7.15 (s, 1H), 2.32 (s, 3H).

Workup

  1. filtrationthe reaction mixture was filtered through a 0.75-in
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3b6ba23f6bd546f68112c609fa0eef4e
Source dataset
uspto-grants-2015_08
Patent number
US09096532B2

Reaction notes

Loading…