Methylamine → HCID 18548949, compound

HRID 276861Notes

Reaction equation

HRID 276861 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][N:15]=[C:16](F)[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:20]#[N:21])[CH:5]=[CH:6][CH:7]=1.[CH3:22][NH2:23]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][N:15]=[C:16]([NH:23][CH3:22])[CH:17]=3)[N:12]=[CH:11][C:10]=2[C:20]#[N:21])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 185489794-(3-Bromo-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile

Product 1

HCID 18548949HCID 18548949, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To 500 mg of 4-(3-bromo-phenylamino)-6-fluoro-[1.7]naphthyridine-3-carbonitrile in 15 mL of absolute ethanol was added 4 mL of 40% aqueous methyl amine. The sealed reaction was heated at 90° C. for 24 hours, stripped of solvents, and purified by flash chromatography on silica gel with a gradient of 0-1% methanol/chloroform followed by purification by preparative thin-layer chromatography with 5% methanol/chloroform to yield 86 mg of 4-(3-bromo-phenylamino)-6-methylamino-[1.7]naphthyridine-3-carbonitrile as an amorphous solid: melting point 250° C. (decomposed); mass spectrum (m/e): M+H 354.1, 356.1.

Workup

  1. customThe sealed reaction
  2. custompurified by flash chromatography on silica gel with a gradient of 0-1% methanol/chloroform
  3. customfollowed by purification by preparative thin-layer chromatography with 5% methanol/chloroform

Sources & evidence

ORD record
ord-57ede612171141c381a7cc2bd1db8f93
Source dataset
uspto-grants-2002_03
Patent number
US06355636B1

Reaction notes

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