Methylamine → HCID 86713673, compound

HRID 1257245Notes

Reaction equation

[NH2:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:11]2[C:12](=[O:24])[N:13]([CH2:22][CH3:23])[C:14]3[C:19]([CH:20]=2)=[CH:18][N:17]=[C:16](Cl)[CH:15]=3)[CH:3]=1.[CH3:25][NH2:26]>>[NH2:1][C:2]1[C:9]([F:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:11]2[C:12](=[O:24])[N:13]([CH2:22][CH3:23])[C:14]3[C:19]([CH:20]=2)=[CH:18][N:17]=[C:16]([NH:26][CH3:25])[CH:15]=3)[CH:3]=1

Participants

Reactant 2

HCID 6329Methylamine

HCID 86713674HCID 86713674, compound

Product 1

HCID 86713673HCID 86713673, compoundYield 61%

Conditions

Temperature: 120 °C

Procedure

A mixture of 4-amino-2-(7-chloro-1-ethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-5-fluorobenzonitrile (420 mg, 1.23 mmol) and methylamine (25%, 50 mL) was heated at 120° C. in a pressure vessel for 1 day. The mixture was cooled to RT, the solid collected via filtration and purified via silica gel chromatography (EtOAc/pet ether) to afford 4-amino-2-(1-ethyl-7-(methylamino)-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-5-fluorobenzonitrile (250 mg, 61% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.42 (s, 1H), 7.81 (s, 1H), 7.72 (s, 1H), 7.53 (d, J=11.6 Hz, 1H), 7.09-7.08 (m, 1H), 6.81 (d, J=8.4 Hz, 1H), 6.23 (s, 2H), 4.16-4.11 (q, J=6.8 Hz, 2H), 2.85 (d, J=4.8 Hz, 3H), 1.22-1.18 (t, J=6.8 Hz, 3H).

Workup

temperatureThe mixture was cooled to RT
filtrationthe solid collected via filtration
custompurified via silica gel chromatography (EtOAc/pet ether)

Sources & evidence

ORD record: ord-a98a7e5a1f774875b1654724b6efbe67
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461179B1

Reaction notes

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