HCID 11379627, compound → HCID 11160262, compound

HRID 1668448Notes

Reaction equation

HRID 1668448 reaction equation
[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-])=O)=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH3:17]>C(O)C.[Pd]>[CH3:1][N:2]([CH3:18])[CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([NH2:14])=[CH:11][CH:12]=2)[CH:7]=[C:6]1[CH3:17]

Participants

4

Reactant 1

HCID 11379627HCID 11379627, compound

Product 1

HCID 11160262HCID 11160262, compoundYield 94.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of compound 23 (0.35 g, 1.415 mmol) in dry ethanol (3 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 24 (0.29 g, 94%) as a syrup. 1H NMR (DMSO-d6) δ 2.18 (s, 6H), 2.32 (s, 3H), 2.42 (t, 2H, J=7.2 Hz), 4.03 (t, 2H, J=7.2 Hz), 4.37 (s, 2H), 5.88 (s, 1H), 6.42 (dd, 1H, J=2.1, 8.4 Hz), 6.56 (d, 1H, J=2.1 Hz), 7.00 (d, 1H, J=8.7 Hz); ESI-MS (m/z, %) 218 (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-f833945b883541e199513e96e7a51f02
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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