7-{5-[4-(6-Cyclopropyl-pyridin-2-yl)-piperazin-1-yl]-pent-1-enyl}-3,4-dihydro-1H-[1,8]naphthyridin-2-one → 7-{5-[4-(6-Cyclopropyl-pyridin-2-yl)-piperazin-1-yl]-pentyl}-3,4-dihydro-1H-[1,8]naphthyridin-2-one

HRID 1373581Notes

Reaction equation

HRID 1373581 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH:19]=[CH:20][C:21]4[N:30]=[C:29]5[C:24]([CH2:25][CH2:26][C:27](=[O:31])[NH:28]5)=[CH:23][CH:22]=4)[CH2:12][CH2:11]3)[CH:7]=[CH:6][CH:5]=2)[CH2:3][CH2:2]1>C1COCC1.[Pd]>[CH:1]1([C:4]2[N:9]=[C:8]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]4[N:30]=[C:29]5[C:24]([CH2:25][CH2:26][C:27](=[O:31])[NH:28]5)=[CH:23][CH:22]=4)[CH2:12][CH2:11]3)[CH:7]=[CH:6][CH:5]=2)[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 694223987-{5-[4-(6-Cyclopropyl-pyridin-2-yl)-piperazin-1-yl]-pent-1-enyl}-3,4-dihydro-1H-[1,8]naphthyridin-2-one

Product 1

HCID 210738897-{5-[4-(6-Cyclopropyl-pyridin-2-yl)-piperazin-1-yl]-pentyl}-3,4-dihydro-1H-[1,8]naphthyridin-2-oneYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

7-{5-[4-(6-Cyclopropyl-pyridin-2-yl)-piperazin-1-yl]-pent-1-enyl}-3,4-dihydro-1H-[1,8]naphthyridin-2-one (0.347 g, 0.831 mmol) was hydrogenated using 20% Pd/C in THF for 15 h. The reaction was filtered and concentrated. Recrystallization from hot CH3CN gave the title compound as a white powder (288 mg, 0.686 mmol, 83%). MS: APCI: M+1: 420.3 (Exact Mass: 419.27).

Workup

  1. customfor 15 h
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated
  4. customRecrystallization from hot CH3CN

Sources & evidence

ORD record
ord-f9d522eb69204a01a636e3f8a711c3d6
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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