Methyl iodide → N-[(4-chlorophenyl)methyl]-6-(3-hydroxyprop-1-ynyl)-1,7-dimethyl-4-oxo-1,8-naphthyridine-3-carboxamide

HRID 1280458Notes

Reaction equation

HRID 1280458 reaction equation
[Cl:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[N:12][C:13]3[C:18]([C:19]=2[OH:20])=[CH:17][C:16]([C:21]#[C:22][CH2:23][OH:24])=[C:15]([CH3:25])[N:14]=3)=[O:9])=[CH:4][CH:3]=1.[C:28](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:19](=[O:20])[C:18]3[C:13](=[N:14][C:15]([CH3:25])=[C:16]([C:21]#[C:22][CH2:23][OH:24])[CH:17]=3)[N:12]([CH3:28])[CH:11]=2)=[O:9])=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178432388HCID 178432388, compound

Product 1

HCID 5276328N-[(4-chlorophenyl)methyl]-6-(3-hydroxyprop-1-ynyl)-1,7-dimethyl-4-oxo-1,8-naphthyridine-3-carboxamideYield 86%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of the N-(4-chlorobenzyl)-4-hydroxy-6-(3-hydroxy-1-propynyl)-7-methyl[1,8]naphthyridine-3-carboxamide (0.081 g, 0.212 mmol) and potassium carbonate (0.117 g, 0.848 mmol) in 5 mL DMF is added methyl iodide (0.036 g, 0.254 mmol). The mixture is stirred at room temperature for 30 min then diluted with water. The resulting precipitate is filtered and dried. The crude solid is triturated with EtOAc-hexanes to yield 0.072 g (86%) of the desired product as a pale yellow solid. Physical characteristics are as follows: m.p. 217-218° C.; 1H NMR (DMSO-d6) δ 10.13, 8.99, 8.46, 7.39, 5.47, 4.55, 4.40, 3.99, 2.75; IR (drift) 3395, 1661, 1604, 1561, 1544, 1503, 1413, 1357, 1261, 1032, 1017, 842, 811, 800, 601 cm−1; MS (EI) m/z (rel. intensity) 395 (M+, 8), 255 (29), 229 (17), 228 (99), 198 (41), 169 (14), 140 (54), 89 (15), 77 (14), 73 (22), 73 (17); HRMS (FAB) calcd for C21H18ClN3O3+H1 396.1115, found 396.1121.

Workup

  1. filtrationThe resulting precipitate is filtered
  2. customdried
  3. customThe crude solid is triturated with EtOAc-hexanes

Sources & evidence

ORD record
ord-3a7bc68cba9c4097a93c6b9d23a2d256
Source dataset
uspto-grants-2002_09
Patent number
US06451811B2

Reaction notes

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