3-(Methylthio)propylamine → HCID 69482268, compound

HRID 2364349Notes

Reaction equation

HRID 2364349 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.[CH3:27][S:28][CH2:29][CH2:30][CH2:31][NH2:32]>>[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:32][CH2:31][CH2:30][CH2:29][S:28][CH3:27])=[O:23])[C:15](=[O:20])[N:16]3[CH3:19])=[N:11][CH:10]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 777433-(Methylthio)propylamineHCID 54730000Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 69482268HCID 69482268, compoundYield 43%

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 and [3-(methylthio)propyl]amine (0.02 mL, 0.589 mmol) was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-N-[3-(methylthio)propyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (15 mg, 43% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.25 (br s, 1 H), 8.57 (s, 1 H), 7.39 (s, 1 H), 7.18-7.14 (m, 2 H), 7.05-7.00 (m, 2 H), 4.14 (s, 2 H), 3.59-3.54 (m, 5 H), 2.59 (m, 2 H), 2.12 (s, 3 H), 1.95 (m, 2 H); HRMS m/z calcd for C21H23FN3O3S: 416.1438. Found: 416.1447.

Sources & evidence

ORD record
ord-5c6bc78751bd4622a2656e6cd4daa2cb
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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