HCID 89647619, compound → HCID 89647472, compound

HRID 1399798Notes

Reaction equation

HRID 1399798 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[C:11]([NH:13][CH2:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][CH:16]=3)[C:10]([N+:25]([O-])=O)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1>CO.[Pd]>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[N:12]=[C:11]([NH:13][CH2:14][C:15]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:18]=[CH:17][CH:16]=3)[C:10]([NH2:25])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 89647619HCID 89647619, compound

Product 1

HCID 89647472HCID 89647472, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 6-morpholino-N-(naphthalen-1-ylmethyl)-3-nitropyridin-2-amine (3.56 g, 9.78 mmol) and 10% Pd/C (300 mg) in MeOH (200 mL) was stirred at room temperature for 3 h under a balloon pressure of H2. It was filtered and the filtrate was concentrated in vacuo to afford the desired as a dark-green solid (3.2 g, 98%); LC/MS: MS (ES+) m/e 335 (MH+); 1H NMR (300 MHz, DMSO-d6) δ ppm 3.10 (t, J=4.5 Hz, 4H), 3.60 (t, J=4.5 Hz, 4H), 4.11 (s, 2H), 4.98 (d, J=5.4 Hz, 2H), 5.79 (d, J=8.1 Hz, 1H), 5.97 (t, J=5.4 Hz, 1H), 6.71 (d, J=8.1 Hz, 1H), 7.42-7.53 (m, 4H), 7.81 (d, J=7.5 Hz, 1H), 7.93 (t, J=4.8 Hz, 1H), 8.21 (d, J=4.8 Hz, 1H).

Workup

  1. filtrationIt was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto afford the

Sources & evidence

ORD record
ord-00769b26af0541d8b86910e21e167c59
Source dataset
uspto-grants-2014_12
Patent number
US08906910B2

Reaction notes

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