Benzoic Acid → HCID 178518099, compound

HRID 916248Notes

Reaction equation

HRID 916248 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][NH:6][C:7]1[S:8][CH2:9][C:10](=[O:12])[N:11]=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.CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[F:16])[CH2:5][NH:6][C:7]1[S:8][C:9](=[CH:27][C:23]2[CH:24]=[CH:25][C:26]3[C:21](=[CH:20][CH:19]=[CH:18][N:17]=3)[N:22]=2)[C:10](=[O:12])[N:11]=1

Participants

8

Reactant 4

HCID 243Benzoic AcidHCID 8082PiperidineHCID 115863361,5-Naphthyridine-2-carbaldehydeHCID 178516941HCID 178516941, compound

Product 1

HCID 178518099HCID 178518099, compoundYield 29.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a suspension of 2-(3-chloro-4-fluoro-benzylamino)-thiazol-4-one (41.4 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 washed with toluene, MeOH and ether to give a brown solid: 32.6 mg (51.1%), which was dissolved in 0.5 mL hot DMF and diluted with water. The precipitates were collected and washed with water, acetone and ether, dried to give 2-(3-chloro-4-fluoro-benzylamino)-5-[1,5]naphthyridin-2-ylmethylene-thiazol-4-one as a light brown solid (18.6 mg, 29.2%). HR-ES (+) m/e calcd. for C19H12ClFN4OS: (M+H)+ 399.0477. Found: 399.0477.

Workup

  1. temperatureThe reaction mixture was then cooled to r.t.
  2. filtrationThe solid was collected by filtration
  3. washwashed with toluene, MeOH and ether
  4. customto give a brown solid
  5. customThe precipitates were collected
  6. washwashed with water, acetone and ether
  7. customdried

Sources & evidence

ORD record
ord-b969d02724404c689cea9cb5037dcb06
Source dataset
uspto-grants-2007_09
Patent number
US07268231B2

Reaction notes

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