HCID 57421471, compound → HCID 57421478, compound

HRID 1668450Notes

Reaction equation

HRID 1668450 reaction equation
[CH3:1][C:2]1[N:3]([CH2:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([N+:11]([O-])=O)=[CH:6][CH:5]=2>C(O)C.[Pd]>[CH3:1][C:2]1[N:3]([CH2:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([NH2:11])=[CH:6][CH:5]=2

Participants

4

Reactant 1

HCID 57421471HCID 57421471, compound

Product 1

HCID 57421478HCID 57421478, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of compound 26 (0.44 g, 1.609 mmol) in dry ethanol (5 mL) was treated with Pd—C (˜0.05 g) and flushed with hydrogen gas. The reaction was stirred under hydrogen atm. for overnight. The reaction was filtered through celite bed, washed with methanol (3×10 mL) and dried to obtain crude compound 27 (0.39 g, quantitative) as a syrup. 1H NMR (DMSO-d6) δ 1.60-1.70 (m, 4H), 2.32 (s, 3H), 2.40-2.48 (m, 4H), 2.60 (t, 2H, J=7.2 Hz), 4.06 (t, 2H, J=7.2 Hz), 4.37 (s, 2H), 5.88 (s, 1H), 6.42 (dd, 1H, J=2.1, 8.7 Hz), 6.56 (d, 1H, J=1.8 Hz), 7.00 (d, 1H, J=8.4 Hz); ESI-MS (m/z, %) 244 (MH+, 100).

Workup

  1. customflushed with hydrogen gas
  2. filtrationThe reaction was filtered through celite bed
  3. washwashed with methanol (3×10 mL)
  4. customdried

Sources & evidence

ORD record
ord-dc21b42899ad41e9aa16b1b48e9e01b6
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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