Methylamine → HCID 86713628, compound

HRID 1430451Notes

Reaction equation

[NH2:1][C:2]1[C:3]([F:23])=[C:4]([C:9]2[C:10](=[O:22])[N:11]([CH2:20][CH3:21])[C:12]3[C:17]([CH:18]=2)=[CH:16][N:15]=[C:14](Cl)[CH:13]=3)[C:5]([Cl:8])=[CH:6][CH:7]=1.[CH3:24][NH2:25]>O1CCOCC1.[Cl-].[Na+].O>[NH2:1][C:2]1[C:3]([F:23])=[C:4]([C:9]2[C:10](=[O:22])[N:11]([CH2:20][CH3:21])[C:12]3[C:17]([CH:18]=2)=[CH:16][N:15]=[C:14]([NH:25][CH3:24])[CH:13]=3)[C:5]([Cl:8])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 3-(3-amino-6-chloro-2-fluorophenyl)-7-chloro-1-ethyl-1,6-naphthyridin-2(1H)-one (0.45 g, 1.150 mmol) in dioxane (5 mL) was treated with methylamine (40% in water, 7.14 g, 92 mmol) and heated at 100° C. overnight. The mixture was cooled to RT, treated with brine and extracted with EtOAc (2×). The combined organics were dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (MeOH/DCM) to afford 3-(3-amino-6-chloro-2-fluorophenyl)-1-ethyl-7-(methylamino)-1,6-naphthyridin-2(1H)-one (350 mg, 88% yield) as a white amorphous solid. 1H NMR (500 MHz, DMSO-d6): δ 8.41 (s, 1H), 7.74 (s, 1H), 7.07 (q, J=4.9 Hz, 1H), 7.03 (dd, J=8.7, 1.3 Hz, 1H), 6.77 (t, J=9.0 Hz, 1H), 6.25 (s, 1H), 5.30 (s, 2H), 4.15-4.13 (q, J=7.0 Hz, 2H), 2.87 (d, J=4.9 Hz, 3H), 1.21 (t, J=7.0 Hz, 3H); MS (ESI) m/z: 347.1 [M+H]+.

Workup

temperatureThe mixture was cooled to RT
extractionextracted with EtOAc (2×)
dry with materialThe combined organics were dried over Na2SO4
concentrationconcentrated to dryness
custompurified via silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record: ord-6f4276635606434cb08d38196f83550f
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940756B2

Reaction notes

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