HCID 178418247, compound → 5-[(8-propan-2-yloxy-1,5-naphthyridin-2-yl)methylidene]-2-(thiophen-2-ylmethylamino)-1,3-thiazol-4-one

HRID 968742Notes

Reaction equation

[CH:1]([O:4][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]=1C#N)([CH3:3])[CH3:2].C(O[Na])(C)=O.C(OC1C=CN=C2C=1N=C(C=C1SC(NC3CC3C3C=CC=CC=3)=NC1=O)C=C2)(C)C>CC(O)=O>[CH:1]([O:4][C:5]1[CH:6]=[CH:7][N:8]=[C:9]2[C:14]=1[N:13]=[C:12]([CH:15]=[C:16]1[S:20][C:19]([NH:21][CH2:22][C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[N:18][C:17]1=[O:28])[CH:11]=[CH:10]2)([CH3:3])[CH3:2]

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 8-isopropoxy-[1,5]naphthyridine-2-carbaldehyde (38.9 mg, 0.18 mmol) (see Example 20) 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, acetone and ether to give 5-(8-isopropoxy-[1,5]naphthyridin-2-ylmethylene)-2-[(thiophen-2-ylmethyl)-amino]-thiazol-4-one as a light brown solid (29.8 mg, 45.4%). HR-ES (+) m/e calcd for C20H18N4O2S2 (M+H)+ 411.0944. found 411.0945.

Workup

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

Sources & evidence

ORD record: ord-74be7b53c5df494cbe8a414eb0377e3d
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07304074B2

Reaction notes

Loading…