6-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile → HCID 178458711, compound

HRID 968720Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]2[S:12][CH2:13][C:14](=[O:16])[N:15]=2)[CH:5]=[CH:6][CH:7]=1.C(O[Na])(C)=O.[CH:22]([C:24]1[N:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[N:30]=[CH:29][C:28]([C:34]#[N:35])=[C:27]2[O:36][CH:37]([CH3:39])[CH3:38])=O>CC(O)=O>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]2[S:12][C:13](=[CH:22][C:24]3[N:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[N:30]=[CH:29][C:28]([C:34]#[N:35])=[C:27]4[O:36][CH:37]([CH3:39])[CH3:38])[C:14](=[O:16])[N:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 2-[2-(3-fluoro-phenyl)-ethylamino]-thiazol-4-one (38.1 mg, 0.16 mmol) (prepared as described below), AcONa (160 mg, 1.95 mmol), and 6-formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile (50.2 mg, 0.21 mmol) (see Example 1) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 80° C. (oil bath) for 5 hrs. The reaction mixture was then cooled to r.t. and triturated with water. The solid was collected by filtration and washed with water. The solid was then suspended in AcOEt (20 mL) and filtered through a glass filter. The solid was washed with AcOEt and dried to give 6-{2-[2-(3-fluoro-phenyl)-ethylamino]-4-oxo-4H-thiazol-5-ylidenemethyl}-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile as a light green solid (30.7 mg, 41.6%). HR-ES (+) m/e calcd for C24H20FN5O2S (M+H)+ 462.1395. found 462.1395.

Workup

temperatureThe reaction mixture was then cooled to r.t.
customtriturated with water
filtrationThe solid was collected by filtration
washwashed with water
filtrationfiltered through a glass
filtrationfilter
washThe solid was washed with AcOEt
customdried

Sources & evidence

ORD record: ord-77f6e892fa994b5f929a4109589a5fe0
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07304074B2

Reaction notes

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