Benzoic Acid → 2-[(5-methylpyrazin-2-yl)methylamino]-5-(1,5-naphthyridin-2-ylmethylidene)-1,3-thiazol-4-one

HRID 916251Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][NH:9][C:10]2[S:11][CH2:12][C:13](=[O:15])[N:14]=2)=[N:6][CH:7]=1.[N:16]1[C:25]2[C:20](=[N:21][C:22]([CH:26]=O)=[CH:23][CH:24]=2)[CH:19]=[CH:18][CH:17]=1.C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:3]=[CH:4][C:5]([CH2:8][NH:9][C:10]2[S:11][C:12](=[CH:26][C:22]3[CH:23]=[CH:24][C:25]4[C:20](=[CH:19][CH:18]=[CH:17][N:16]=4)[N:21]=3)[C:13](=[O:15])[N:14]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a suspension of 2-[(5-methyl-pyrazin-2-ylmethyl)-amino]-thiazol-4-one (35.6 mg, 0.16 mmol), and 1,5-naphthyridine-6-carboxaldehyde (31.6 mg, 0.2 mmol) in toluene (1 mL) in a microwave tube were added benzoic acid (2.0 mg, 0.02 mmol) and piperidine (1.7 uM, 0.02 mmol). The reaction mixture was heated to 130° C. with microwave for 10 min., then cooled to r.t. and diluted with toluene. The solid was collected by filtration and washed with toluene, MeOH and ether to give 2-[(5-methyl-pyrazin-2-ylmethyl)-amino]-5-[1,5] naphthyridin-2-ylmethylene-thiazol-4-one as a brown solid (10.6 mg, 18.3%). HR-ES (+) m/e calcd. for C18H14N6OS: (M+H)+ 363.1023. Found: 363.1022.

Workup

temperaturecooled to r.t.
filtrationThe solid was collected by filtration
washwashed with toluene, MeOH and ether

Sources & evidence

ORD record: ord-14f156cdf70149f0a9b003258519afff
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268231B2

Reaction notes

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