1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86629725, compound

HRID 656831Notes

Reaction equation

HRID 656831 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:19](=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23])[CH2:18][C@:8]1([C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]1=[O:17])[CH2:7]2.C1(P([N:39]=[N+:40]=[N-:41])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>CN(C=O)C>[N:39]([CH2:2][CH2:3][C:4]1[CH:5]=[C:6]2[C:19](=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23])[CH2:18][C@:8]1([C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]1=[O:17])[CH2:7]2)=[N+:40]=[N-:41]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 67173148HCID 67173148, compound

Product 1

HCID 86629725HCID 86629725, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of (2S)-5-(2-hydroxyethyl)-6-nitro-1,3-dihydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one from Step E (174 mg, 0.54 mmol) in DMF (4 mL) were added diphenyl phosphoryl azide (177 mg, 0.64 mmol) and DBU (0.096 mL, 0.64 mmol). The mixture was heated at 100° C. for 6 h, then quenched with H2O (20 mL) and extracted with EtOAc (50 mL). The organic layer was dried over Na2 SO4, filtered, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2 Cl2:MeOH—100:0 to 80:20, to give the title compound. MS: m/z=351 (M−1).

Workup

  1. customquenched with H2O (20 mL)
  2. extractionextracted with EtOAc (50 mL)
  3. customThe organic layer was dried over Na2 SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of CH2 Cl2

Sources & evidence

ORD record
ord-944c4037b2e44e118921c2ba67b33b58
Source dataset
uspto-grants-2011_12
Patent number
US08071772B2

Reaction notes

Loading…