Triethylamine → HCID 69480938, compound

HRID 2364341Notes

Reaction equation

HRID 2364341 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](OCC)=[O:22])[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl.[CH3:35][S:36]([CH2:39][CH2:40][NH2:41])(=[O:38])=[O:37]>>[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]([NH:41][CH2:40][CH2:39][S:36]([CH3:35])(=[O:38])=[O:37])=[O:22])[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 17749886Ethanamine, 2-(methylsulfonyl)-, hydrochloride (1:1)HCID 54730000Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69480938HCID 69480938, compoundYield 30.2%

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 (0.05 mL, 0.364 mmol) and [2-(methylsulfonyl)ethyl]amine hydrochloride (174 mg, 1.08 mmol) was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-N-[2-(methylsulfonyl)ethyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (11 mg, 22% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.61 (br s, 1 H), 8.56 (s, 1 H), 7.39 (s, 1 H), 7.16-7.12 (m, 2 H), 7.04-6.99 (m, 2 H), 4.13 (s, 2 H), 3.95 (m, 2 H), 3.57 (s, 3 H), 3.37 (m, 2 H), 2.98 (s, 3 H); MS m/z 434 (M+1).

Sources & evidence

ORD record
ord-5a398589d3d74fa2b2339248b3a507ac
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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