6-[[2-[(3-methylthiophen-2-yl)methylamino]-4-oxo-1,3-thiazol-5-ylidene]methyl]-4-propan-2-yloxy-1,5-naphthyridine-3-carbonitrile → HCID 178429645, compound

HRID 968728Notes

Reaction equation

CC1C=CSC=1CNC1SCC(=O)N=1.C(O[C:19]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([CH:29]=[C:30]3[S:34][C:33]([NH:35][CH2:36][C:37]4[S:38][CH:39]=[CH:40][C:41]=4[CH3:42])=[N:32][C:31]3=[O:43])[N:27]=2)[N:22]=[CH:21][C:20]=1[C:44]#[N:45])(C)C.O=C1C(=CC2N=C3C(=CC=2)N=CC(C#N)=C3)SC(NCC2SC=CC=2)=N1>CC(O)=O>[CH3:42][C:41]1[CH:40]=[CH:39][S:38][C:37]=1[CH2:36][NH:35][C:33]1[S:34][C:30](=[CH:29][C:26]2[N:27]=[C:28]3[C:23](=[CH:24][CH:25]=2)[N:22]=[CH:21][C:20]([C:44]#[N:45])=[CH:19]3)[C:31](=[O:43])[N:32]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 2-[(3-methyl-thiophen-2-ylmethyl)-amino]-thiazol-4-one (21.7 mg, 0.10 mmol), AcONa (160 mg, 1.95 mmol) (see Example 5), and 6-formyl-[1,5]naphthyridine-3-carbonitrile (22.0 mg, 0.12 mmol) (see Example 11) in a sealed tube was added AcOH (0.3 mL). The reaction mixture was heated to 100° C. (oil bath) for 1.5 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-[(3-methyl-thiophen-2-ylmethyl)-amino]-4-oxo-4H-thiazol-5-ylidenemethyl}-[1,5]naphthyridine-3-carbonitrile as a light brown solid (14.0 mg, 35.8%). HR-ES (+) m/e calcd for C19H13N5OS2 (M+H)+ 414.0454. found 414.0452.

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-9c409334352143518122fe0675cb3c19
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07304074B2

Reaction notes

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