1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 23000173, compound

HRID 397490

Reaction equation

HRID 397490 reaction equation
O[CH2:2][C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[CH:8][NH:9][C:5]=2[CH:4]=1.C1C=CC(P([N:26]=[N+:27]=[N-:28])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[N:26]([CH2:2][C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[CH:8][NH:9][C:5]=2[CH:4]=1)=[N+:27]=[N-:28]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 135055565-(Hydroxymethyl)-1H-benzimidazole

Product 1

HCID 23000173HCID 23000173, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C.) suspension of 5-(hydroxymethyl)-benzimidazole (920 mg, 6.2 mmol) in THF (12 mL) was added sequentially DPPA (1.46 mL, 6.8 mmol) and DBU (1.11 mL, 7.4 mmol). The resulting solution was heated to reflux for 5 h, cooled to RT, and concentrated in vacuo. The residue was partitioned between sodium bicarbonate and ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo. Silica gel chromatography (15% MeOH—CHCl3), afforded the title compound as a brown solid: Rf (8:1:1 EtOAc-MeOH—NH4H)=0.31; m.p. 110-114° C.; 1H NMR (400 MHz, DMSO-d6): δ8.25 (s, 1H), 7.27 (d, J=8.4, 1H), 7.62-7.60 (m, 2H), 7.20 (d, J=8.2 Hz, 1H), 8.24 (s, 1H); HRMS (FAB) C8H8N5 calcd. 174.1847 (M+1). Found 174.1222.

Workup

  1. temperatureTo a cooled
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 5 h
  4. concentrationconcentrated in vacuo
  5. customThe residue was partitioned between sodium bicarbonate and ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c08cae394226432fbd6efad8e8611001
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Linked notes

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