Benzoic Acid → HCID 178518103, compound

HRID 916249Notes

Reaction equation

HRID 916249 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][C:8]1[S:9][CH2:10][C:11](=[O:13])[N:12]=1.[N:14]1[C:23]2[C:18](=[N:19][C:20]([CH:24]=O)=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1.C(O)(=O)C1C=CC=CC=1.N1CCCCC1>C1(C)C=CC=CC=1>[N:19]1[C:18]2[C:23](=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:22]=[CH:21][C:20]=1[CH:24]=[C:10]1[S:9][C:8]([NH:7][CH2:6][C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[N:12][C:11]1=[O:13]

Participants

6

Reactant 4

HCID 243Benzoic AcidHCID 8082PiperidineHCID 115863361,5-Naphthyridine-2-carbaldehydeHCID 178516942HCID 178516942, compound

Product 1

HCID 178518103HCID 178518103, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
120 °C

Procedure

To a suspension of 2-[(thiophen-2-ylmethyl)-amino]-thiazol-4-one (34.0 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 120° C. with microwave for 5 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 5-[1,5]naphthyridin-2-ylmethylene-2-[(thiophen-2-ylmethyl)-amino]-thiazol-4-one as a light brown solid (19.7 mg, 34.9%). HR-ES (+) m/e calcd. for C17H12N4OS2: (M+H)+ 353.0526. Found: 353.0526.

Workup

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

Sources & evidence

ORD record
ord-9331586058ec4218bcd06bb04da52e8a
Source dataset
uspto-grants-2007_09
Patent number
US07268231B2

Reaction notes

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