HCID 66894469, compound → HCID 22478924, compound

HRID 252747Notes

Reaction equation

HRID 252747 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:31])[C:10]1[CH:15]=[CH:14][C:13]([CH:16]=[CH:17][C:18]2[N:23]=[C:22]([NH2:24])[N:21]=[C:20]([N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[N:19]=2)=[CH:12][CH:11]=1>CO.[Pd]>[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:31])[C:10]1[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][C:18]2[N:23]=[C:22]([NH2:24])[N:21]=[C:20]([N:25]3[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]3)[N:19]=2)=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 66894469HCID 66894469, compound

Product 1

HCID 22478924HCID 22478924, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 223 (18 mg, 0.043 mmol) in MeOH (5 mL) was added 10% Pd/C (10 mg, 0.021 mmol). The reaction mixture was shaked under a pressure of H2 (40 psi) at room temperature for 16 h using an hydrogenation apparatus. Then, the reaction mixture was purged with N2, filtered through celite, and concentrated. The crude residue was then purified by flash chromatography on silica gel (MeOH/CH2Cl2: 2/98→4/96) to afford the title compound 224 (10 mg, 0.024 mmol, 56% yield). 1H NMR (300 MHz, CDCl3—CD3OD) δ (ppm): 7.82 (d, J=8.1 Hz, 2H), 7.35 (d, J=8.1 Hz, 2H), 7.08 (t, J=7.0 Hz, 1H), 6.89-6.79 (m, 2H), 7.80-6.90 (m, 1H), 3.76 (s, 4H), 3.13 (t, J=8.1 Hz, 2H), 2.88 (t, J=8.1 Hz, 2H), 1.90-1.40 (m, 10H).

Workup

  1. customThen, the reaction mixture was purged with N2
  2. filtrationfiltered through celite
  3. concentrationconcentrated
  4. customThe crude residue was then purified by flash chromatography on silica gel (MeOH/CH2Cl2: 2/98→4/96)

Sources & evidence

ORD record
ord-4161981ddbb64d3d8c7b074f54d94aab
Source dataset
uspto-grants-2011_01
Patent number
US07868204B2

Reaction notes

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