HCID 15453463, compound → HCID 15453460, compound

HRID 380605Notes

Reaction equation

HRID 380605 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:13][C:14]2[NH:15][CH2:16][CH2:17][N:18]=2)[CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2)([CH3:3])=[CH2:2]>CO.[Pd]>[CH:1]([C:4]1[CH:5]=[C:6]([NH:13][C:14]2[NH:15][CH2:16][CH2:17][N:18]=2)[CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 15453463HCID 15453463, compound

Product 1

HCID 15453460HCID 15453460, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 7-isopropenyl-5-(2-imidazolin-2-ylamino)indole (0.25 g, 1.0 mmol) and 10% Pd/C (100 mg) in 10 mL of MeOH was stirred for 12 h under H2 (18 psi). The reaction mixture was filtered and concentrated in vacuo, yielding an oil which, in NMR analysis, was highly pure and corresponds to the desired product. The product obtained was converted to the succinate salt and recrystallized from isopropanol-CHCl3 to afford 0.13 g of the product as a light brown solid: mp 254-255° C.; H NMR (CD3OD) δ7.28 (d, J=1.8 Hz, 1H), 7.27 (d, J=3.2 Hz, 1H), 6.82 (d, J=1.8 Hz, 1H), 6.43 (d, J=3.2 Hz, 1H), 3.67 (s, 4H), 3.30 (hep, 1H), 2.18 (s, 3H); Anal. Calc. for C14H18N4.1.0C4H6O4 requires C, 60.32; H, 6.19; N, 15.63. Found: C, 60.17; H, 6.25; N, 15.59.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customyielding an oil which

Sources & evidence

ORD record
ord-7ab4a24758ff4f71a7aaaefa36fd852d
Source dataset
uspto-grants-2001_10
Patent number
US06303643B1

Reaction notes

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