HCID 24990697, compound → HCID 24990699, compound

HRID 222135Notes

Reaction equation

HRID 222135 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8]3[C:14]([C:15]([NH2:17])=[O:16])=[C:13]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[N:12]([CH3:24])[C:9]=32)=[CH:4][N:3]=1>[Pd]>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([N:11]=1)=[C:9]1[N:12]([CH3:24])[C:13]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[C:14]([C:15]([NH2:17])=[O:16])[C:8]1=[CH:7][CH:6]=2

Participants

3

Reactant 1

HCID 24990697HCID 24990697, compound

Product 1

HCID 24990699HCID 24990699, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of 8-amino-1-methyl-2-phenyl-4,5-dihydro-1H-1,7,9-triaza-cyclopenta[a]naphthalene-3-carboxylic acid amide N4 (0.25 mmol) and 10% Pd on carbon (50 mg) in 10 mL of xilene was heated to reflux for 15 days. The mixture was filtered through a celite pad and the solvent evaporated to dryness affording the title compound (85% yield). ESI (+) MS: m/z 318 (MH+). 1H NMR: 4.21 (s, 3H), 6.15 (bs, 1H), 6.76 (bs, 2H), 7.08 (bs, 1H), 7.42 (d, J=8.50, 1H), 7.52-7.65 (m, 5H), 7.83 (d, J=8.50, 1H), 9.03 (s, 1H).

Workup

  1. temperatureto reflux for 15 days
  2. filtrationThe mixture was filtered through a celite pad
  3. customthe solvent evaporated to dryness

Sources & evidence

ORD record
ord-9956480e95f44c15afd194553d22d65c
Source dataset
uspto-grants-2012_06
Patent number
US08207180B2

Reaction notes

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