HCID 15453463, compound → HCID 15453460, compound

HRID 617257Notes

Reaction equation

HRID 617257 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) δ 7.28 (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-d08f04cd2d8941f4b5ffd28c7ea34b17
Source dataset
uspto-grants-1999_09
Patent number
US05948804

Reaction notes

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