Benzoic Acid → HCID 178518087, compound

HRID 916246Notes

Reaction equation

HRID 916246 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][NH:5][C:6]1[S:7][CH2:8][C:9](=[O:11])[N:10]=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.CN(C=O)C.O>[Cl:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[CH2:4][NH:5][C:6]1[S:7][C:8](=[CH:26][C:22]2[CH:23]=[CH:24][C:25]3[C:20](=[CH:19][CH:18]=[CH:17][N:16]=3)[N:21]=2)[C:9](=[O:11])[N:10]=1

Participants

8

Reactant 4

HCID 243Benzoic AcidHCID 8082PiperidineHCID 115863361,5-Naphthyridine-2-carbaldehydeHCID 178516939HCID 178516939, compound

Product 1

HCID 178518087HCID 178518087, compoundYield 37.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

To a suspension of 2-(2-chloro-benzylamino)-thiazol-4-one (77.0 mg, 0.32 mmol), and 1,5-naphthyridine-6-carboxaldehyde (63.2 mg, 0.40 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 150° C. with microwave for 10 min. and then cooled to r.t. The solid was filtered off, washed with toluene to give a brown solid, which was dissolved in 1 mL hot DMF and diluted with water. The precipitates were collected and washed with water, acetone and ether, dried to give 2-(2-chloro-benzylamino)-5-[1,5] naphthyridin-2-ylmethylene-thiazol-4-one as a light brown solid (45.6 mg, 37.4%). HR-ES (+) m/e calcd. for C19H13ClN4OS: (M+H)+ 381.0572. Found: 381.0572.

Workup

  1. temperaturecooled to r.t
  2. filtrationThe solid was filtered off
  3. washwashed with toluene
  4. customto give a brown solid, which
  5. customThe precipitates were collected
  6. washwashed with water, acetone and ether
  7. customdried

Sources & evidence

ORD record
ord-6123e585736d477ba7243cd0b65f11d2
Source dataset
uspto-grants-2007_09
Patent number
US07268231B2

Reaction notes

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