HCID 69422410, compound → HCID 21073877, compound

HRID 1373588Notes

Reaction equation

HRID 1373588 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH:18]=[CH:19][C:20]2[N:29]=[C:28]3[C:23]([C:24]([CH3:31])=[CH:25][C:26](=[O:30])[NH:27]3)=[CH:22][CH:21]=2)[CH2:11][CH2:10]1>C1COCC1.O.CCO.[Ni]>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]2[N:29]=[C:28]3[C:23]([C:24]([CH3:31])=[CH:25][C:26](=[O:30])[NH:27]3)=[CH:22][CH:21]=2)[CH2:11][CH2:10]1

Participants

6

Reactant 1

HCID 69422410HCID 69422410, compound

Product 1

HCID 21073877HCID 21073877, compoundYield 88.4%

Reagents, catalysts & solvents 4

HCID 935NickelCatalyst2×HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

7-{5-[4-(2,3-Dichloro-phenyl)-piperazin-1-yl]-pent-1-enyl}-4-methyl-1H-[1,8]naphthyridin-2-one (880 mg, 1.92 mmol) was dissolved in THF (50 mL) and added to a Parr bottle containing a suspension of Raney-Nickel (1.5 mL of a settled suspension in water) in EtOH (50 mL). The mixture was hydrogenated at 45 psi for 5.5 h. The reaction was not complete so additional Raney-Nickel (1 mL of a suspension in water) was added and the mixture was hydrogenated at 45 psi for 2.5 h. The reaction mixture was filtered through a bed of Celite and washed with EtOH. The filtrate was concentrated to give a white solid. Purification by column chromatography (10% MeOH/EtOAc) afforded the title compound as a white solid (780 mg, 88%). mp 195–196° C.; 1H NMR (CDCl3, 400 MHz): δ 9.16 (br s, 1H), 7.88 (d, 1H), 7.18–7.12 (m, 2H), 7.06 (d, 1H), 7.00–6.92 (m, 1H), 6.50 (s, 1H), 3.14–3.00 (m, 4H), 2.85 (t, 2H), 2.72–2.54 (m, 4H), 2.46 (d, 3H), 2.42 (t, 2H), 1.85–1.72 (m, 2H), 1.64–1.52 (m, 2H), 1.48–1.36 (m, 2H); MS ES: m/z=459.08, 461.03.

Workup

  1. additionadded to a Parr bottle
  2. additioncontaining
  3. additionwas added
  4. waitthe mixture was hydrogenated at 45 psi for 2.5 h
  5. filtrationThe reaction mixture was filtered through a bed of Celite
  6. washwashed with EtOH
  7. concentrationThe filtrate was concentrated
  8. customto give a white solid
  9. customPurification by column chromatography (10% MeOH/EtOAc)

Sources & evidence

ORD record
ord-4be95b17b799457a9255a03e06e18ade
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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