6-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile → HCID 178458710, compound

HRID 968717Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8]1[S:9][CH2:10][C:11](=[O:13])[N:12]=1.C(O[Na])(C)=O.[CH:19]([C:21]1[N:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[N:27]=[CH:26][C:25]([C:31]#[N:32])=[C:24]2[O:33][CH:34]([CH3:36])[CH3:35])=O>CC(O)=O>[CH:34]([O:33][C:24]1[C:23]2[C:28](=[CH:29][CH:30]=[C:21]([CH:19]=[C:10]3[S:9][C:8]([NH:7][CH2:6][C:2]4[S:1][CH:5]=[CH:4][CH:3]=4)=[N:12][C:11]3=[O:13])[N:22]=2)[N:27]=[CH:26][C:25]=1[C:31]#[N:32])([CH3:36])[CH3:35]

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of 2-[(thiophen-2-ylmethyl)-amino]-thiazol-4-one (34.0 mg, 0.16 mmol, (prepared as described below), AcONa (160 mg, 1.95 mmol), and 6-formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile (57.9 mg, 0.24 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. The solid was washed with AcOEt and dried to give 4-isopropoxy-6-{4-oxo-2-[(thiophen-2-ylmethyl)-amino]-4H-thiazol-5-ylidenemethyl}-[1,5]naphthyridine-3-carbonitrile as a light brown solid (35.4 mg, 50.8%). HR-ES (+) m/e calcd for C21H17N5O2S2 (M+H)+ 436.0897. found 436.0895.

Workup

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

Sources & evidence

ORD record: ord-d4ce85bc08af42538acb3aeea76f94d5
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07304074B2

Reaction notes

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