1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 18475857, compound

HRID 2187893Notes

Reaction equation

HRID 2187893 reaction equation
[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH2:13]O)=[CH:11][N:10]=[CH:9]2)=[CH:5][C:4]=1[F:17])#[N:2].C1C=CC(P([N:32]=[N+:33]=[N-:34])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[N:32]([CH2:13][C:12]1[N:8]([CH2:7][C:6]2[CH:15]=[CH:16][C:3]([C:1]#[N:2])=[C:4]([F:17])[CH:5]=2)[CH:9]=[N:10][CH:11]=1)=[N+:33]=[N-:34]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 185360621-(4-Cyano-3-fluorobenzyl)-5-(hydroxymethyl)imidazole

Product 1

HCID 18475857HCID 18475857, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(4-cyano-3-fluorobenzyl)-5-(hydroxymethyl)imidazole, as described above in Example 4, Step F, (103 mg, 0.45 mmol) in dry THF (1 mL), at 0° C., under argon, were added DPPA (147 mg, 0.53 mmol) then DBU (75 mg, 0.49 mmol). The mixture was allowed to warm to ambient temperature and then stirred for 3 hrs. The mixture was then partitioned between H2O (10 mL) and CH2Cl2 (20 mL). The aqueous layer was extracted further with CH2Cl2 (2×15 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with a gradient of CHCl3-1% MeOH −0.1% NH4OH to CHCl3-5% MeOH −0.5% NH4OH, to yield the titled product.

Workup

  1. customThe mixture was then partitioned between H2O (10 mL) and CH2Cl2 (20 mL)
  2. extractionThe aqueous layer was extracted further with CH2Cl2 (2×15 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash column chromatography on silica
  7. washeluting with a gradient of CHCl3-1% MeOH −0.1% NH4OH to CHCl3-5% MeOH −0.5% NH4OH

Sources & evidence

ORD record
ord-fd85b0be43c8446cb3fd0102aa355799
Source dataset
uspto-grants-2002_06
Patent number
US06410534B1

Reaction notes

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