6-Morpholinonicotinic Acid → 6-Morpholin-4-yl-N-(2-oxazol-2-yl-4-oxo-1-phenyl-1,4-dihydro-[1,8]naphthyridin-3-yl-methyl)-nicotinamide

HRID 1887840Notes

Reaction equation

HRID 1887840 reaction equation
[NH2:1][CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:4]=1[C:20]1[O:21][CH:22]=[CH:23][N:24]=1.[N:25]1([C:31]2[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][N:32]=2)[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>>[N:25]1([C:31]2[CH:39]=[CH:38][C:34]([C:35]([NH:1][CH2:2][C:3]3[C:12](=[O:13])[C:11]4[C:6](=[N:7][CH:8]=[CH:9][CH:10]=4)[N:5]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C:4]=3[C:20]3[O:21][CH:22]=[CH:23][N:24]=3)=[O:36])=[CH:33][N:32]=2)[CH2:26][CH2:27][O:28][CH2:29][CH2:30]1

Participants

3

Reactant 2

HCID 27764606-Morpholinonicotinic AcidHCID 712085053-(aminomethyl)-2-(oxazol-2-yl)-1-phenyl-1,8-naphthyridin-4(1H)-one

Product 1

HCID 712087986-Morpholin-4-yl-N-(2-oxazol-2-yl-4-oxo-1-phenyl-1,4-dihydro-[1,8]naphthyridin-3-yl-methyl)-nicotinamide

Procedure

6-Morpholin-4-yl-N-(2-oxazol-2-yl-4-oxo-1-phenyl-1,4-dihydro-[1,8]naphthyridin-3-yl-methyl)-nicotinamide was prepared starting from intermediate B and 6-morpholin-4-yl-nicotinic acid. 1H NMR (300 MHz, DMSO-d6) δ ppm 8.65-8.67 (m, 2H) 8.48 (d, J=2.90 Hz, 1H) 8.05-8.15 (m, 1H) 7.98 (d, J=0.75 Hz, 1H) 7.85 (dd, J=8.70, 2.90 Hz, 1H) 7.55 (dd, J=8.20, 4.40 Hz, 1H) 7.23-7.45 (m, 5H) 7.18 (d, J=0.75 Hz, 1H) 6.79 (d, J=8.30 Hz, 1H) 4.25 (d, J=4.20 Hz, 2H) 3.62-3.73 (m, 4H) 3.47-3.57 (m, 4H).

Sources & evidence

ORD record
ord-7e336f7fb97e44ef8b7f69c12a13c62f
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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