HCID 11605821, compound → HCID 44417989, compound

HRID 1986626Notes

Reaction equation

HRID 1986626 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:35])[N:11]([CH2:25][CH2:26][CH2:27][N:28]2[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]2)[CH:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][C:16]([N+:22]([O-])=O)=[CH:17][CH:18]=3)[CH2:13]2)[CH:5]=[CH:6][C:7]=1[F:8]>CCO.[Ni]>[NH2:22][C:16]1[CH:15]=[C:14]2[C:19]([CH2:20][CH2:21][CH:12]([N:11]([CH2:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]3)[C:10]([NH:9][C:4]3[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=3)=[O:35])[CH2:13]2)=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 11605821HCID 11605821, compound

Product 1

HCID 44417989HCID 44417989, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-(3-chloro-4-fluoro-phenyl)-1-[3-(4-methyl-piperazin-1-yl)-propyl]-1-(7-nitro-1,2,3,4-tetrahydro-naphthalen-2-yl)-urea (from Preparative Example 26, 0.286 g, 0.57 mmol) in absolute EtOH (10 mL) was added Raney Ni (˜50 mg). The mixture was hydrogenated using a Parr hydrogenator at 50 psi for 2 hours, then filtered through Celite, and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatography by eluting with 5% MeOH/CH2Cl2 to give 0.200 g (75%) of 1-(7-amino-1,2,3,4-tetrahydro-naphthalen-2-yl)-3-(3-chloro-4-fluoro-phenyl)-1-[3-(4-methyl-piperazin-1-yl)-propyl]-urea as a light brown solid. 1H NMR (300 MHz, CD3OD): δ 7.57 (dd, 1H), 7.31 (m, 1H), 7.15 (t, 1H), 6.84 (d, 1H), 6.53 (dd, 1H), 6.48 (d, 1H), 4.30 (m, 1H), 3.38 (t, 2H), 2.95 (m, 1H), 2.82 (m, 3H), 2.60-2.35 (m, 10H), 2.26 (s, 3H), 1.96 (m, 2H), 1.85 (m, 2H). MS-ESI: 474.1 (M+H+).

Workup

  1. customfor 2 hours
  2. filtrationfiltered through Celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by silica gel chromatography
  5. washby eluting with 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-c3843ed61c78438f88e4cb6e15778e2e
Source dataset
uspto-grants-2009_06
Patent number
US07550467B2

Reaction notes

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