Acetonitrile--water (1/1) → HCID 53794639, compound

HRID 1601092Notes

Reaction equation

HRID 1601092 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][C:2]=1[CH2:10][N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[CH2:20][N:21]([CH3:43])[CH2:22][C:23]([C:25]1[CH:42]=[CH:41][C:28]([O:29][CH2:30][C:31]([O:33]CC2C=CC=CC=2)=[O:32])=[CH:27][CH:26]=1)=[O:24].CC#N.O>CO.[Pd]>[N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[NH:1][C:2]=1[CH2:10][N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[C:12]1[CH2:20][N:21]([CH3:43])[CH2:22][C:23]([C:25]1[CH:26]=[CH:27][C:28]([O:29][CH2:30][C:31]([OH:33])=[O:32])=[CH:41][CH:42]=1)=[O:24]

Participants

5

Reactant 2

HCID 18373917Acetonitrile--water (1/1)HCID 54135925HCID 54135925, compound

Product 1

HCID 53794639HCID 53794639, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 4-[2-[[[1-[(benzimidazol-2-yl)methyl]benzimidazol-2-yl]methyl]methylamino]acetyl]phenoxyacetate (0.08 g, 0.18 mmol) and 5% Pd/C (0.11 g) in MeOH (15 mL) was shaken on a Parr apparatus under H2 (41 psi) for 1 h. The mixture was filtered through a bed of celite®, and the filter pad was washed with glacial AcOH and MeOH. The filtrate was concentrated to give the crude product (0.07 g). Preparative HPLC (Hamilton PRP-1® column, step gradient, 10-30% CH3CN/H2O containing 0.1% TFA) afforded the title compound: MS (ES) m/e 484.2 [M+H]+. Anal. Calcd for C27H25N504 .3 C2HF3O2 : C, 48.01; H, 3.42 N, 8.48. Found: C, 48.40; H, 3.72; N, 8.77.

Workup

  1. filtrationThe mixture was filtered through a bed of celite®
  2. washthe filter pad was washed with glacial AcOH and MeOH
  3. concentrationThe filtrate was concentrated
  4. customto give the crude product (0.07 g)

Sources & evidence

ORD record
ord-3626e09c1d3a411baeff3b7f5414a08c
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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