Triphenylphosphine → HCID 86591620, compound

HRID 1295717Notes

Reaction equation

HRID 1295717 reaction equation
[CH3:1][CH2:2]OC(/N=N/C(OCC)=O)=O.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][N:23]([C:26]2[C:27]([O:32]CCO)=[N:28][CH:29]=[CH:30][N:31]=2)[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[C:36]([C:38]1[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=1)#[N:37].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[C:36]([C:38]1[CH:43]=[CH:42][C:41]([O:44][CH2:1][CH2:2][N:28]2[CH:29]=[CH:30][N:31]=[C:26]([N:23]3[CH2:22][CH2:21][N:20]([C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[CH2:25][CH2:24]3)[C:27]2=[O:32])=[CH:40][CH:39]=1)#[N:37]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 130194-CyanophenolHCID 5462977Diethyl azodicarboxylateHCID 114160742-[3-(4-Tert-butoxycarbonyl-1-piperazinyl)-2-pyrazinyloxy]ethanol

Product 1

HCID 86591620HCID 86591620, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DEAD (0.520 ml, 3.3 mmol) was added to a slurry of 2-[3-(4-tert-butoxycarbonyl-1-piperazinyl)-pyrazinyloxy]ethanol (1.00 g, 3.08 mmol), 4-cyanophenol (0.381 g, 3.20 mmol) and resin bound triphenylphosphine (1.1 g, 3.3 mmol) in dichloromethane (10 mL) and shaken overnight. The reaction mixture was filtered, concentrated and purified by chromatography on silica gel using toluene/EtOAc (1:1) as eluent to give 0.168 g (13%) of the title compound. 1H NMR and MS analyses support the stated structure. HRMS m/z calcd for C22H27N5O4 (M)+ 425.2063, found 425.2075.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. custompurified by chromatography on silica gel

Sources & evidence

ORD record
ord-0e7165db57854397961cc91e0c7babc3
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

Loading…