Acetonitrile → HCID 22181354, compound

HRID 1796487Notes

Reaction equation

HRID 1796487 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([CH:14]([OH:16])[CH3:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH3:26])=[CH:20][CH:19]=2)[CH2:3][CH2:2]1.C[N+]1([O-])CCOCC1.C(#N)C>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:14](=[O:16])[CH3:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH3:26])=[CH:20][CH:19]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 82029Methyl morpholine oxide2×HCID 22181397HCID 22181397, compound

Product 1

HCID 22181354HCID 22181354, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture 1-[1-(cyclopropylmethyl)-2-(4-ethoxybenzyl)-1H-benzimidazol-5-yl]ethanol (1.35 g, 3.86 mmol), N-methylmorpholine-N-oxide (0.497 g, 4.24 mmol) and 4 Å molecular sieves (2.0 g) in CH2Cl2 (10 mL) was added tetrapropylammonium perruthenate (0.068 g, 0.193 mmol) and the resulting mixture was stirred at room temperature for 90 minutes. N-methylmorpholine-N-oxide (0.124 g, 1.06 mmol) and acetonitrile (1 mL) were added and the mixture was stirred at room temperature overnight. The solvent was concentrated in vacuo and the crude product was purified by silica gel column chromatography (30% EtOAc/hexanes to 60% EtOAc/hexanes) to provide the title compound (0.880 g, 65%) as a white solid. 1H NMR (CDCl3): δ 8.34 (s, 1H), 7.94 (dd, J=8.4 Hz, J=2.0 Hz, 1H), 7.35 (d, J=8.4 Hz, 1H), 7.15 (d, J=8.4 Hz, 2H), 6.91 (dd, J=6.4 Hz, J=2.0 Hz, 2H), 4.29 (s, 2H), 3.98 (q, J=7.2 Hz, 2H) 3.41 (d, J=6.8 Hz, 2H), 2.67 (s, 3H), 1.38 (t, J=7.0 Hz, 3H), 1.07–1.00 (m, 1H), 0.55–0.51 (m, 2H), 0.29–0.26 (m, 2H). 13C NMR (CDCl3): δ 198.71, 159.01, 156.43, 143.29, 140.01, 132.68, 130.44, 128.67, 123.50, 121.95, 115.83, 110.73, 64.38, 49.23, 34.63, 27.63, 15.76, 11.99, 5.20. MS (ESI) (M+H)+=349. Anal. Calcd for C22H24N2O2+0.1H2O: C, 75.44, H, 6.96; N, 8.00. Found: C, 75.48; H, 7.13; N, 8.01.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. concentrationThe solvent was concentrated in vacuo
  3. customthe crude product was purified by silica gel column chromatography (30% EtOAc/hexanes to 60% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ed4dca9a0af24694ac1db1c0536882ee
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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