HCID 18967512, compound → HCID 23353485, compound

HRID 235144Notes

Reaction equation

HRID 235144 reaction equation
[N+:1]([C:4]1[C:5]([NH:10][C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][CH:17]=[C:18]3[CH:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)=[CH:13][CH:12]=2)=[N:6][CH:7]=[CH:8][CH:9]=1)([O-])=O>[Pd].C(O)C.C(OCC)(=O)C>[NH2:1][C:4]1[C:5]([NH:10][C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][CH:17]=[C:18]3[CH:21]3[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]3)=[CH:13][CH:12]=2)=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 1

HCID 18967512HCID 18967512, compound

Product 1

HCID 23353485HCID 23353485, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product from Example 58 (0.18 g, 0.5 mmol) and 10% palladium on carbon (0.04 g)in ethanol (35 mL) and ethyl acetate (15 mL) was hydrogenated at 45 psi for 4 hours. The mixture was filtered through celite and concentrated to give 7-(3-amino-2-pyridylamino)-1-(1-methyl-4-piperidinyl)-naphthalene which was suitable for further reaction; 1H NMR δ 8.07 (d, J=2 Hz, 1 H), 7.89 (dd, J=1.5, 5 Hz, 1 H), 7.79 (d, J=9 Hz, 1 H), 7.64 (d, J=7.5 Hz, 1 H), 7.45 (dd, J=2, 9 Hz, 1 H), 7.36-7.26 (m, 2H with CHCl3 from NMR solvent overlapping), 7.07 (dd, J=1.5, 7.5 Hz, 1 H), 6.82 (dd, J=5, 7.5 Hz, 1 H), 6.51 (br s, 1 H), 3.49 (br s, 2 H), 3.18 (tt, J=4, 12 Hz, 1H), 3.03 (long range coupled d, J=13.5 Hz, 2 H), 2.39 (s, 3 H), 2.23 (dt, J=2.5, 11.5 Hz, 2H), 2.08-1.87 (m, 4 H). HRMS m/e calculated for C21H24N4 : 332.1996. Observed m/e 332.2003.

Workup

  1. filtrationThe mixture was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-63dcf72debde4668ae4d2da40f2ac567
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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