(5Z)-5-[(3-cyclopentyloxy-4-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one → 6-(2-amino4-oxo4H-thiazol-5-ylidenemethyl)-[1,5]naphthyridine-3-carbonitrile

HRID 968729Notes

Reaction equation

COC1C=CC(/C=C2/C(NC(S/2)=N)=O)=CC=1OC1CCCC1.C(O[Na])(C)=O.[O:28]=[C:29]1[C:33](=[CH:34][C:35]2[N:36]=[C:37]3[C:42](=[CH:43][CH:44]=2)[N:41]=[CH:40][C:39]([C:45]#[N:46])=[CH:38]3)[S:32][C:31]([NH:47]CC2SC=CC=2)=[N:30]1>CC(O)=O>[NH2:47][C:31]1[S:32][C:33](=[CH:34][C:35]2[N:36]=[C:37]3[C:42](=[CH:43][CH:44]=2)[N:41]=[CH:40][C:39]([C:45]#[N:46])=[CH:38]3)[C:29](=[O:28])[N:30]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a mixture of pseudothiohydantoin (Aldrich, 97%, 23.2 mg, 0.20 mmol), AcONa (160 mg, 1.95 mmol), molecular sieves, and 6-formyl-[1,5]naphthyridine-3-carbonitrile (38.5 mg, 0.21 mmol) (see Example 11) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 120° C. for 3.5 hrs. The reaction mixture was then cooled to r.t. and triturated with water. The solid was collected by filtration and washed with water, AcOEt and ether to give 6-(2-amino-4-oxo-4H-thiazol-5-ylidenemethyl)-[1,5]naphthyridine-3-carbonitrile as a yellowish solid (30.3 mg, 44.6%). LR-ES (+) m/e 282 (M+H).

Workup

temperatureThe reaction mixture was then cooled to r.t.
customtriturated with water
filtrationThe solid was collected by filtration
washwashed with water, AcOEt and ether

Sources & evidence

ORD record: ord-e8255c44a0d94864a1e9104ca618c4d3
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07304074B2

Reaction notes

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