1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 59829664, compound

HRID 551135Notes

Reaction equation

HRID 551135 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:20][CH:21]([C:23]2[O:24][C:25]([CH2:28][N:29]([CH3:31])[CH3:30])=[CH:26][CH:27]=2)O)=[CH:11][C:12]([Cl:19])=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P([N:46]=[N+:47]=[N-:48])(C2C=CC=CC=2)=O)C=CC=CC=1.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1.CN(C)C=O.[Br-].[Li+]>[N:46]([CH:21]([C:23]1[O:24][C:25]([CH2:28][N:29]([CH3:31])[CH3:30])=[CH:26][CH:27]=1)[CH2:20][C:10]1[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:18]2[C:13]([CH:14]=[CH:15][CH:16]=[N:17]2)=[C:12]([Cl:19])[CH:11]=1)=[N+:47]=[N-:48]

Participants

7

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 59829674HCID 59829674, compound

Product 1

HCID 59829664HCID 59829664, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 82050Lithium BromideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 2-[8-(benzyloxy)-5-chloroquinolin-7-yl]-1-{5-[(dimethylamino)methyl]-2-furyl}ethanol (2.18 mmol) in toluene (13.5 mL) and dimethylformamide (2.7 mL) at 0° C. was added diphenyl phosphoryl azide (5.46 mmol, 2.5 eq.) followed by dropwise addition of 1,8-diazabicyclo[5.4.0]undec-7-ene (5.46 mmol, 2.5 eq.). The reaction mixture was stirred 5 min at 0° C. then warmed to room temperature and stirred 16 h. The mixture was next diluted with saturated aqueous lithium bromide solution (25 mL) and extracted with ethyl acetate (3×15 mL). The combined organic layers were dried (MgSO4), filtered and concentrated to a dark brown syrup that was purified by column chromatography using 30% acetone/dichloromethane to give the product as a brown syrup (1.65 mmol, 76%). MS (ESI) m/z 462.4; HRMS: calcd for C25H24ClN5O2+H+, 462.16913; found (ESI, [M+H]+ Obs'd), 462.1693.

Workup

  1. temperaturethen warmed to room temperature
  2. stirringstirred 16 h
  3. extractionextracted with ethyl acetate (3×15 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to a dark brown syrup that
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-90535f54d501464f99d7e275e01bf87a
Source dataset
uspto-grants-2011_05
Patent number
US07947712B2

Reaction notes

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