1-[4-Fluoro-2-(methylsulfanyl)phenyl]methanamine → HCID 22346460, compound

HRID 897355Notes

Reaction equation

HRID 897355 reaction equation
[OH:1][C:2]1[C:3]([C:23]([O:25]C)=O)=[N:4][C:5]([N:12]([CH3:22])[S:13]([C:16]2[N:17]=[CH:18][N:19]([CH3:21])[CH:20]=2)(=[O:15])=[O:14])=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[F:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][NH2:35])=[C:30]([S:36][CH3:37])[CH:29]=1>C1(C)C=CC=CC=1>[F:27][C:28]1[CH:33]=[CH:32][C:31]([CH2:34][NH:35][C:23]([C:3]2[C:2]([OH:1])=[C:11]3[C:6]([CH:7]=[CH:8][CH:9]=[N:10]3)=[C:5]([N:12]([CH3:22])[S:13]([C:16]3[N:17]=[CH:18][N:19]([CH3:21])[CH:20]=3)(=[O:14])=[O:15])[N:4]=2)=[O:25])=[C:30]([S:36][CH3:37])[CH:29]=1

Participants

4

Reactant 2

HCID 167539431-[4-Fluoro-2-(methylsulfanyl)phenyl]methanamineHCID 68898245HCID 68898245, compound

Product 1

HCID 22346460HCID 22346460, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of methyl 8-hydroxy-5-{methyl[(1-methyl-1H-imidazol-4-yl) sulfonyl]amino}-1,6-naphthyridine-7-carboxylate. (0.14 g, 0.371 mmol) and 1-[4-fluoro-2-(methylthio)phenyl]methanamine (0.102 g, 0.594 mmol) in toluene (1 mL) were heated at 130 C in a sealed tube for 72 hr. The solvent was evaporated in vacuo. The residue was purified by preparative HPLC (Waters PrepPak Column, C18 eluting with 5-95% acetonitrile/water (0.1% TFA) at 100 ml/min) to afford the title compound after lyophilization.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customThe residue was purified by preparative HPLC (Waters PrepPak Column, C18 eluting with 5-95% acetonitrile/water (0.1% TFA) at 100 ml/min)

Sources & evidence

ORD record
ord-09bf1b25b34a48b19edeee05f45eaac8
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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