HCID 67190803, compound → HCID 86238174, compound

HRID 545091Notes

Reaction equation

HRID 545091 reaction equation
[N+:1]([C:4]1[C:5]([NH2:21])=[N:6][CH:7]=[CH:8][C:9]=1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]=1)([O-])=O>CO.[Pd]>[F:20][C:17]([F:18])([F:19])[C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:9]2[CH:8]=[CH:7][N:6]=[C:5]([NH2:21])[C:4]=2[NH2:1])=[N:12][CH:13]=1

Participants

4

Reactant 1

HCID 67190803HCID 67190803, compound

Product 1

HCID 86238174HCID 86238174, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Hydrogenate a mixture of 3-nitro-N4-(5-(trifluoromethyl)pyridin-2-yl)pyridine-2,4-diamine (1.1 g, 0.00368 moles) and 10% Pd/C (150 mg) in 50 mL of MeOH at room temperature under 50 psi of H2 (g). After 17 hours, filter the mixture through Celite, and wash the Celite well with MeOH. Concentrate the filtrate under vacuum to give the title compound as a brown solid. 1H NMR (400 MHz, DMSO-D6) δ 8.81 (s, 1H), 8.41 (s, 1H), 7.819 (d, 1H, J=2.2 Hz), 7.273 (d, 1H, J=1.9 Hz), 6.885 (d, 2H, J=1.9 Hz), 5.685 (bs, 2H), 4.575 (bs, 2H). Mass spec. (270.04, M+H).

Workup

  1. filtrationfilter the mixture through Celite
  2. washwash the Celite well with MeOH
  3. concentrationConcentrate the filtrate under vacuum

Sources & evidence

ORD record
ord-eb08ce85f6b44744b65e5a0a2275dd3b
Source dataset
uspto-grants-2011_05
Patent number
US07935702B2

Reaction notes

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