6-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile → HCID 178458709, compound

HRID 968721Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 2-(2-chloro-4-fluoro-benzylamino)-thiazol-4-one (41.4 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, re-filtered through a paper filter to give 6-[2-(2-chloro-4-fluoro-benzylamino)-4-oxo-4H-thiazol-5-ylidenemethyl]-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile as a light brown solid (19.2 mg, 24.9%). HR-ES (+) m/e calcd for C23H17FClN5O2S (M+H)+ 482.0849. found 482.0848.

Workup

temperatureThe reaction mixture was then cooled to r.t.
customtriturated with water
filtrationThe solid was collected by filtration
washwashed with water
filtrationre-filtered through a paper
filtrationfilter

Sources & evidence

ORD record: ord-60169f0a2b16412c96b88da43d03d871
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07304074B2

Reaction notes

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