Benzoic Acid → HCID 178518118, compound

HRID 916250Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]2[S:12][CH2:13][C:14](=[O:16])[N:15]=2)[CH:5]=[CH:6][CH:7]=1.[N:17]1[C:26]2[C:21](=[N:22][C:23]([CH:27]=O)=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1.C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][NH:10][C:11]2[S:12][C:13](=[CH:27][C:23]3[CH:24]=[CH:25][C:26]4[C:21](=[CH:20][CH:19]=[CH:18][N:17]=4)[N:22]=3)[C:14](=[O:16])[N:15]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a suspension of 2-[2-(3-fluoro-phenyl)-ethylamino]-thiazol-4-one (38.1 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-[2-(3-fluoro-phenyl)-ethylamino]-5-[1,5]naphthyridin-2-ylmethylene-thiazol-4-one as a brown solid (22.3 mg, 36.9%). HR-ES (+) m/e calcd. for C20H15FN4OS: (M+H)+ 379.1024. Found: 379.1024.

Workup

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

Sources & evidence

ORD record: ord-20fcff506c314a4f956082f20a234cf4
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268231B2

Reaction notes

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