Benzoic Acid → HCID 178429644, compound

HRID 916247Notes

Reaction equation

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

Participants

Conditions

Temperature: 130 °C

Procedure

To a suspension of 2-[(3-methyl-thiophen-2-ylmethyl)-amino]-thiazol-4-one (36.2 mg, 0.16 mmol), and 1,5-naphthyridine-6-carboxaldehyde (31.6 mg, 0.20 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. The reaction mixture was then cooled to r.t. and diluted with toluene. The solid was collected by filtration and the solid was washed with toluene, MeOH and ether to give 2-[(3-Methyl-thiophen-2-ylmethyl)-amino]-5-[1,5]naphthyridin-2-ylmethylene-thiazol-4-one as a light brown solid (25.7 mg, 43.9%). HR-ES (+) m/e calcd. for C18H14N4OS2: (M+H)+ 367.0682. Found: 367.0683.

Workup

temperatureThe reaction mixture was then cooled to r.t.
filtrationThe solid was collected by filtration
washthe solid was washed with toluene, MeOH and ether

Sources & evidence

ORD record: ord-f66e45354a6d4d6bb963beb64ae480a1
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268231B2

Reaction notes

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