6-Formyl-[1,5]naphthyridine-3-carbonitrile → HCID 178510297, compound

HRID 968724Notes

Reaction equation

C(O[C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH:15]=[C:16]3[S:20][C:19]([NH:21][CH2:22][C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)=[N:18][C:17]3=[O:28])[N:13]=2)[N:8]=[CH:7][C:6]=1[C:29]#[N:30])(C)C.C(O[Na])(C)=O.C(C1N=C2C(=CC=1)N=CC(C#N)=C2)=O>CC(O)=O>[O:28]=[C:17]1[C:16](=[CH:15][C:12]2[N:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:29]#[N:30])=[CH:5]3)[S:20][C:19]([NH:21][CH2:22][C:23]2[S:24][CH:25]=[CH:26][CH:27]=2)=[N:18]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 2-[(thiophen-2-ylmethyl)-amino]-thiazol-4-one one (34.0 mg, 0.16 mmol) (see Example 4), AcONa (160 mg, 1.95 mmol), and 6-formyl-[1,5]naphthyridine-3-carbonitrile (38.5 mg, 0.21 mmol) (prepared as described below) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 100° C. (oil bath) for 4.5 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 dissolved in DMF (1 mL) with heating and then poured into ice water, and filtered. The solid was washed with AcOEt and dried to give 6-{4-oxo-2-[(thiophen-2-ylmethyl)-amino]-4H-thiazol-5-ylidenemethyl}-[1,5]naphthyridine-3-carbonitrile as a dark brown solid (12.8 mg, 21.2%). HR-ES (+) m/e calcd for C18H11N5OS2 (M+H)+ 400.0297. found 400.0298.

Workup

temperatureThe reaction mixture was then cooled to r.t.
customtriturated with water
filtrationThe solid was collected by filtration
washwashed with water
dissolutionThe solid was then dissolved in DMF (1 mL)
temperaturewith heating
additionpoured into ice water
filtrationfiltered
washThe solid was washed with AcOEt
customdried

Sources & evidence

ORD record: ord-d56cb615fd744070ae77d0be09e10156
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07304074B2

Reaction notes

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