3-Chlorophenol → {4-[5-(3-Chlorophenoxy)-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl]-phenyl}-(4-methylpiperazin-1-yl)methanone

HRID 659457Notes

Reaction equation

HRID 659457 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.[Cl:27][C:28]1[CH:29]=[C:30](O)[CH:31]=[CH:32][CH:33]=1>CO.C(Cl)Cl>[Cl:27][C:28]1[CH:33]=[C:32]([CH:31]=[CH:30][CH:29]=1)[O:1][CH:2]1[CH2:11][CH2:10][NH:9][C:8]2[N:7]=[CH:6][C:5]([C:12]3[CH:13]=[CH:14][C:15]([C:18]([N:20]4[CH2:21][CH2:22][N:23]([CH3:26])[CH2:24][CH2:25]4)=[O:19])=[CH:16][CH:17]=3)=[CH:4][C:3]1=2

Participants

4

Reactant 2

HCID 79333-ChlorophenolHCID 57886094[4-(5-Hydroxy-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl)phenyl]-(4-methylpiperazin-1-yl)methanone

Product 1

HCID 57886076{4-[5-(3-Chlorophenoxy)-5,6,7,8-tetrahydro-[1,8]naphthyridin-3-yl]-phenyl}-(4-methylpiperazin-1-yl)methanoneYield 50%

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-chlorophenol (21.8 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 (50% yield). LCMS: m/z=463.12 (M+H+), 1H-NMR (CDCl3, 400 MHz) δ 2.00-2.12 (m, 1H), 2.27-2.33 (m, 1H), 2.33 (s, 3H), 2.34-2.6 (m, 4H), 3.4-3.7 (m, 4H), 3.7-3.9 (m, 2H), 5.18 (bs, 1H), 5.38 (t, J=3.6 Hz, 1H), 6.91 (dd, J=1.6 and 8.3 Hz, 1H), 6.99-7.04 (m, 2H), 7.23-7.27 (m, 1H), 7.43-7.50 (m, 4H), 7.61 (d, J=2.0 Hz), 8.30 (d, J=2.2 Hz).

Sources & evidence

ORD record
ord-874ee7f1626940dd926b822694c44f4f
Source dataset
uspto-grants-2011_12
Patent number
US08080561B2

Reaction notes

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