HCID 59394995, compound → HCID 59394992, compound

HRID 383364Notes

Reaction equation

HRID 383364 reaction equation
[C:1](=[O:27])([O:25][CH3:26])[O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:6]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH3:19])[CH2:14][CH2:13]2)=[CH:5][C:4]=1[CH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>C(O)C.[Pd]>[C:1](=[O:27])([O:25][CH3:26])[O:2][C:3]1[CH:8]=[C:7]([NH2:9])[C:6]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH3:19])[CH2:14][CH2:13]2)=[CH:5][C:4]=1[CH:20]1[CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

4

Reactant 1

HCID 59394995HCID 59394995, compound

Product 1

HCID 59394992HCID 59394992, compoundYield 80.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-cyclopentyl-4-(4-ethylpiperazin-1-yl)-5-nitrophenyl methyl carbonate (675 mg, 1.79 mmol) in ethanol (7 mL) treated with 10% Pd/C (68 mg) was stirred under H2 atmosphere for 3 h. The reaction mixture filtered through a plug of silica and washed with methanol. The filtrate was concentrated in vacuo to yield 5-amino-2-cyclopentyl-4-(4-ethylpiperazin-1-yl)phenyl methyl carbonate (500 mg, 80% yield). 1H NMR (400.0 MHz, DMSO-d6) δ 6.83 (d, J=8.4 Hz, 1H), 6.57 (d, J=8.4 Hz, 1H), 4.86 (s, 2H), 3.83 (s, 3H), 2.93-2.82 (m, 5H), 2.62 (d, J=9.4 Hz, 2H), 2.36 (q, J=7.2 Hz, 2H), 2.23-2.20 (m, 2H), 1.82-1.81 (m, 2H), 1.69-1.66 (m, 2H), 1.58-1.55 (m, 2H), 1.42-1.39 (m, 2H), 1.01 (t, J=7.1 Hz, 3H).

Workup

  1. filtrationThe reaction mixture filtered through a plug of silica
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e38c093909ad4b97bff13436867ec0d2
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

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