2,2,2-Trifluoro-1-(4-nitro-10-aza-tricyclo[6.3.2.0*2,7*]trideca-2,4,6-trien-10-yl)-ethanone → 1-(4-Amino-10-aza-tricyclo[6.3.2.0*2,7*]trideca-2,4,6-trien-10-yl)-2,2,2-trifluoro-ethanone

HRID 1040766Notes

Reaction equation

HRID 1040766 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]([N:5]1[CH2:15][CH:14]2[CH2:16][CH2:17][CH:7]([C:8]3[C:13]2=[CH:12][C:11]([N+:18]([O-])=O)=[CH:10][CH:9]=3)[CH2:6]1)=[O:4]>CO.C(O)(=O)C.[Pd]>[NH2:18][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH:7]1[CH2:17][CH2:16][CH:14]2[CH2:15][N:5]([C:3](=[O:4])[C:2]([F:22])([F:1])[F:21])[CH2:6]1

Participants

5

Reactant 1

HCID 865961892,2,2-Trifluoro-1-(4-nitro-10-aza-tricyclo[6.3.2.0*2,7*]trideca-2,4,6-trien-10-yl)-ethanone

Product 1

HCID 111968611-(4-Amino-10-aza-tricyclo[6.3.2.0*2,7*]trideca-2,4,6-trien-10-yl)-2,2,2-trifluoro-ethanoneYield 100%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

2,2,2-Trifluoro-1-(4-nitro-10-aza-tricyclo[6.3.2.0*2,7*]trideca-2,4,6-trien-10-yl)-ethanone (1.227 g, 3.91 mmol) was placed in methanol (100 mL) and acetic acid (1 mL). 10% Palladium on carbon (6.8 mg) was then added. The reaction was hydrogenated at 20 psi for 30 minutes. The mixture was then filtered through celite and concentrated under reduced pressure to obtain 1-(4-amino-10-aza-tricyclo[6.3.2.0*2,7*]trideca-2,4,6-trien-10-yl)-2,2,2-trifluoro-ethanone as a brown oil (1.110 g, 100%). LCMS (m/e) 285 (M+1); 1H-NMR (CDCl3, 400 MHz) δ 6.92 (dd, 1H, J=8.0 and 10.9 Hz), 6.60-6.50 (m, 2H), 4.23-4.10 (m, 1H), 3.90-3.75 (m, 1H), 3.46-3.25 (m, 2H), 3.15-3.00 (m, 2H), 2.03-1.91 (m, 2H), 1.80-1.70 (m, 2H).

Workup

  1. filtrationThe mixture was then filtered through celite and
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a405d8f1afc04eeda92a9b64e650da70
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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