Triethylamine → 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-N-{2-[4-(methylsulfonyl)phenyl]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364343Notes

Reaction equation

HRID 2364343 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:26])=[C:14]([C:21]([O:23]CC)=O)[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:34][S:35]([C:38]1[CH:43]=[CH:42][C:41]([CH2:44][CH2:45][NH2:46])=[CH:40][CH:39]=1)(=[O:37])=[O:36]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]2[CH:18]=[C:17]3[C:12]([C:13]([OH:26])=[C:14]([C:21]([NH:46][CH2:45][CH2:44][C:41]4[CH:40]=[CH:39][C:38]([S:35]([CH3:34])(=[O:37])=[O:36])=[CH:43][CH:42]=4)=[O:23])[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 27609572-(4-Methanesulfonylphenyl)ethan-1-amineHCID 54730000Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 694815067-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-N-{2-[4-(methylsulfonyl)phenyl]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 26%

Procedure

In a similar manner to that described in example 196, from ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (30 mg, 0.084 mmol) described in example 92, triethylamine (0.5 mL, 4.08 mmol), and {2-[4-(methylsulfonyl)phenyl]ethyl}amine (250 mg, 1.25 mmol), was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-N-{2-[4-(methylsulfonyl)phenyl]ethyl}-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (11 mg, 26% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.28 (br s, 1 H), 8.56 (s, 1 H), 7.87 (d, J=8 Hz, 2 H), 7.44 (d, J=8 Hz, 2 H), 7.38 (s, 1 H), 7.16-7.14 (m, 2 H), 7.04-6.99 (m, 2 H), 4.13 (s, 2 H), 3.72 (m, 2 H), 3.56 (s, 3 H), 3.06-3.02 (m, 5 H); HRMS m/z calcd for: C26H25FN3O5S: 510.1493. Found: 510.1498.

Sources & evidence

ORD record
ord-1cfb17544d054f18a6f010fd1d7b9b0a
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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