3-Hydroxypyridine → (4-Methylpiperazin-1-yl)-{4-[5-(pyridine-3-yloxy)-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl]phenyl}methanone

HRID 2074680Notes

Reaction equation

HRID 2074680 reaction equation
[OH:1][CH:2]1[CH2:11][CH2:10][NH:9][C:8]2[N:7]=[CH:6][C:5]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([N:20]4[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]4)=[O:19])=[CH:14][CH:13]=3)=[CH:4][C:3]1=2.O[C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1>CO.C(Cl)Cl>[CH3:26][N:23]1[CH2:22][CH2:21][N:20]([C:18]([C:15]2[CH:14]=[CH:13][C:12]([C:5]3[CH:6]=[N:7][C:8]4[NH:9][CH2:10][CH2:11][CH:2]([O:1][C:28]5[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=5)[C:3]=4[CH:4]=3)=[CH:17][CH:16]=2)=[O:19])[CH2:25][CH2:24]1

Participants

4

Reactant 2

HCID 79713-HydroxypyridineHCID 57886094[4-(5-Hydroxy-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)phenyl]-(4-methylpiperazin-1-yl)methanone

Product 1

HCID 57885855(4-Methylpiperazin-1-yl)-{4-[5-(pyridine-3-yloxy)-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl]phenyl}methanoneYield 20%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

[4-(5-Hydroxy-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)phenyl]-(4-methylpiperazin-1-yl)methanone (20 mg) was reacted with 3-hydroxypyridine (16.2 mg) as in General Procedure 12. Silica gel chromatography using a gradient of 0-15% methanol/CH2Cl2 as the eluting solvent gave the title compound as a yellow foam (20% yield). LCMS: m/z=430.17 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 2.02-2.12 (m, 1H), 2.30-2.34 (m, 1H), 2.33 (s, 3H), 2.34-2.56 (m, 4H), 3.40-3.70 (m, 4H), 3.70-3.90 (m, 2H), 5.24 (bs, 1H), 5.44 (t, J=3.5 Hz, 1H), 7.26-7.29 (m, 1H), 7.31-7.37 (m, 1H), 7.41-7.50 (m, 4H), 7.58 (d, J=2.0 Hz, 1H), 8.28-8.33 (m, 2H), 8.43 (d, J=2.5 Hz, 1H).

Sources & evidence

ORD record
ord-6b97166bffad499ab7116520b2e607cd
Source dataset
uspto-grants-2011_04
Patent number
US07919502B2

Reaction notes

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