HCID 69488497, compound → HCID 69488974, compound

HRID 968640Notes

Reaction equation

HRID 968640 reaction equation
[CH:1]1([CH2:7][N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][C:15]=3[N+:17]([O-])=O)[C:10]([C:20]([N:22]3[CH2:27][CH2:26][N:25]([CH2:28][CH3:29])[CH2:24][CH2:23]3)=[O:21])=[CH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[NH2:17][C:15]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:16]=1[N:8]([CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)[CH:9]=[C:10]2[C:20]([N:22]1[CH2:23][CH2:24][N:25]([CH2:28][CH3:29])[CH2:26][CH2:27]1)=[O:21]

Participants

4

Reactant 1

HCID 69488497HCID 69488497, compound

Product 1

HCID 69488974HCID 69488974, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

4-{[1-(Cyclohexylmethyl)-7-nitro-1H-indol-3-yl]carbonyl}-1-ethylpiperazine (200 mg, 0.5 mmol) was dissolved in methanol (10 ml) to which was added palladium (5 wt. % on activated carbon; 50 mg, cat.) as a slurry in methanol (3 ml). The system was then sealed and flushed with nitrogen before fixing a hydrogen source (balloon). The mixture was stirred at room temperature under hydrogen for 15 hours after which it was filtered through celite and concentrated. The resulting brown oil was purified by flash chromatography using 95% dichloromethane, 5% methanol as eluent to yield the title product as the free base. 1H NMR (400 MHz, CD3OD) δH 0.97-1.08 (2H, m), 1.12 (3H, t, J 7.5), 1.17-1.26 (3H, m), 1.53 (2H, d, J 12.5), 1.63-1.75)(3H m) 1.87-1.98 (1H, m), 2.44-2.55 (6H, m), 3.37 (4H, t, J 5.0), 4.20 (2H, d, J 7.5), 6.59 (1H, dd, J 7.5, 1.0), 6.93 (1H, t, J 7.5), 7.06 (1H, dd, J 8.0, 1.0), 7.39 (1H, s); EIMS: m/z=369.0 [M+H]+.

Workup

  1. customThe system was then sealed
  2. customflushed with nitrogen
  3. filtrationwas filtered through celite and
  4. concentrationconcentrated
  5. customThe resulting brown oil was purified by flash chromatography

Sources & evidence

ORD record
ord-85340135177740478fb1b54b4c7043fc
Source dataset
uspto-grants-2007_12
Patent number
US07304064B2

Reaction notes

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