1-Amino-2-propanol → 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364287Notes

Reaction equation

HRID 2364287 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH:16]=3)[C:11]([OH:26])=[C:10]([C:27](OCC)=[O:28])[C:9]2=[O:32])=[CH:4][CH:3]=1.[NH2:33][CH2:34][CH:35]([OH:37])[CH3:36]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([CH2:18][C:19]4[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=4)[CH:16]=3)[C:11]([OH:26])=[C:10]([C:27]([NH:33][CH2:34][CH:35]([OH:37])[CH3:36])=[O:28])[C:9]2=[O:32])=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 41-Amino-2-propanolHCID 59799019Ethyl 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 694828131-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 75%

Procedure

In a similar manner to that described in example 196, from ethyl 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (20 mg, 0.043 mmol) and 1-amino-2-propanol (0.05 mL) was prepared 1-(4-fluorophenyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-N-(2-hydroxypropyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (15 mg, 75% yield) as a white solid. 1H NMR (CDCl3) δ 10.22 (br s, 1 H), 8.53 (s, 1 H), 7.31-7.25 (m, 2 H), 7.22-7.18 (m, 2 H), 7.03-6.92 (m, 4 H), 6.72 (s, 1 H), 4.03 (m, 1 H), 3.94 (s, 2 H), 3.56 (m, 1 H), 3.36 (m, 1 H), 1.24 (d, J=6.4 Hz, 3 H). MS m/z 466 (M+1).

Sources & evidence

ORD record
ord-c3bc1aa366cf485e93986bf2c872d541
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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