N-(2-aminoethyl)-N'-methylthiourea → 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-N-(2-{[(methylamino)carbonothioyl]amino}ethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide

HRID 2364295Notes

Reaction equation

HRID 2364295 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.[NH2:27][CH2:28][CH2:29][NH:30][C:31]([NH:33][CH3:34])=[S: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:27][CH2:28][CH2:29][NH:30][C:31]([NH:33][CH3:34])=[S:32])=[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 12953274N-(2-aminoethyl)-N'-methylthioureaHCID 54730000Ethyl 7-[(4-Fluorophenyl)methyl]-4-hydroxy-1-methyl-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

Product 1

HCID 866127807-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-N-(2-{[(methylamino)carbonothioyl]amino}ethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamideYield 33%

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 (10 mg, 0.028 mmol) described in example 92 and N-(2-aminoethyl)-N′-methylthiourea (48 mg, 0.364 mmol), was prepared 7-[(4-fluorophenyl)methyl]-4-hydroxy-1-methyl-N-(2-{[(methylamino)carbonothioyl]amino}ethyl)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide(4 mg, 33% yield) as a white solid after purification by reverse phase HPLC. 1H NMR (CDCl3) δ 10.55 (br s, 1 H), 8.56 (s, 1 H), 7.40 (s, 1 H), 7.24-7.15 (m, 2 H), 7.05-7.00 (m, 2 H), 6.79 (br s, 1 H), 6.19 (br s, 1 H), 4.14 (s, 2 H), 3.75-3.70 (m, 4 H), 3.56 (s, 3 H), 2.95 (s, 3 H); HRMS m/z calcd for C21H23N5O3FS: 444.1506 Found: 444.1532.

Sources & evidence

ORD record
ord-bb4399c14db24304a639769bb4da0480
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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