HCID 86711984, compound → HCID 71002262, compound

HRID 2281062Notes

Reaction equation

HRID 2281062 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:16]4[CH:30]=[CH:29][C:19]([CH2:20][N:21]5[CH2:25][C:24](=[O:26])[N:23]([CH3:27])[C:22]5=[O:28])=[CH:18][CH:17]=4)=[C:13]([CH:14]=[CH2:15])[C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1>CCO.[Pd]>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:16]4[CH:30]=[CH:29][C:19]([CH2:20][N:21]5[CH2:25][C:24](=[O:26])[N:23]([CH3:27])[C:22]5=[O:28])=[CH:18][CH:17]=4)=[C:13]([CH2:14][CH3:15])[C:8]=3[N:7]=[N:6]2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 86711984HCID 86711984, compound

Product 1

HCID 71002262HCID 71002262, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1-{4-[1-(cyclopropylmethyl)-4-ethenyl-1H-benzotriazol-5-yl]benzyl}-3-methylimidazolidine-2,4-dione (68 mg, 0.17 mmol) in EtOH (1.7 mL) was added palladium on carbon (10 wt %, 9 mg). The mixture was sparged under an atmosphere of hydrogen (1 atm) and stirred for 18 hours. The mixture was filtered through Celite and washed with ethanol. The filtrate was concentrated in vacuo and purified via reverse phase HPLC (5-95% MeCN/water+0.1% TFA) to provide the title compound: 1H NMR (400 MHz, CDCl3) 7.31-7.43 (m, 6H), 4.65 (s, 2H), 4.53 (d, 2H, J=6.8 Hz), 3.83 (s, 2H), 3.13 (q, 2H, J=7.6 Hz), 3.09 (s, 3H), 1.40-1.48 (m, 1H), 1.26 (t, 3H, J=7.2 Hz), 0.66-0.71 (m, 2H), 0.50-0.54 (m, 2H) ppm. LRMS m/z (M+H) 404.3 found, 404.2 required.

Workup

  1. customThe mixture was sparged under an atmosphere of hydrogen (1 atm)
  2. filtrationThe mixture was filtered through Celite
  3. washwashed with ethanol
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified via reverse phase HPLC (5-95% MeCN/water+0.1% TFA)

Sources & evidence

ORD record
ord-be77931b669f43489114dcdb6388f467
Source dataset
uspto-grants-2015_09
Patent number
US09139576B2

Reaction notes

Loading…