HCID 59004670, compound → HCID 59004615, compound

HRID 1668452Notes

Reaction equation

HRID 1668452 reaction equation
[CH3:1][C:2]1[N:3]([CH2:14][CH2:15][CH:16]2[CH2:20][CH2:19][CH2:18][N:17]2[CH3:21])[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][CH:16]2[CH2:20][CH2:19][CH2:18][N:17]2[CH3:21])[C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([NH2:11])=[CH:6][CH:5]=2

Participants

4

Reactant 1

HCID 59004670HCID 59004670, compound

Product 1

HCID 59004615HCID 59004615, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of compound 29 (0.5 g, 1.739 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 (3×15 mL) and dried to obtain crude compound 31 (0.34 g, 77%) as a syrup. 1H NMR (DMSO-d6) δ 1.40-1.67 (m, 4H), 1.82-1.93 (m, 2H), 1.98-2.10 (m, 2H), 2.18 (s, 3H), 2.31 (s, 3H), 2.90-2.96 (m, 1H), 3.97 (t, 2H, J=7.5 Hz), 4.39 (s, 2H), 5.88 (s, 1H), 6.43 (dd, 1H, J=2.1, 8.4 Hz), 6.57 (d, 1H, J=1.8 Hz), 7.00 (d, 1H, J=8.7 Hz); ESI-MS (m/z, %) 258 (MH+, 28), 161 (100).

Workup

  1. customflushed with hydrogen gas
  2. filtrationThe reaction was filtered through celite bed
  3. washwashed with methanol (3×15 mL)
  4. customdried

Sources & evidence

ORD record
ord-7cb1ccd28ee546719584288bcd9d1f8a
Source dataset
uspto-grants-2011_08
Patent number
US07989447B2

Reaction notes

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