p-Toluenesulfonic acid → HCID 117775045, compound

HRID 2201555Notes

Reaction equation

HRID 2201555 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O.CC1C=CC(S(O)(=O)=O)=CC=1>CCO>[Cl:11][C:9]1[CH:8]=[CH:7][C:3]2[C:4](=[O:5])[NH:6][CH:16]([C:15]3[CH:18]=[CH:19][CH:20]=[C:13]([F:12])[CH:14]=3)[NH:1][C:2]=2[N:10]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 680093-FluorobenzaldehydeHCID 226076432-Amino-6-chloropyridine-3-carboxamide

Product 1

HCID 117775045HCID 117775045, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-amino-6-chloronicotinamide (200 mg, 1.17 mmol) and 3-fluorobenzaldehyde (160 mg, 1.29 mmol) in 20 mL of EtOH was added PTSA (20 mg, 0.12 mmol), and then the mixture was heated at reflux for 16 h. The solution was cooled to room temperature and filtered to give the product of 7-chloro-2-(3-fluorophenyl)-2,3-dihydropyrido[2,3-d]pyrimidin-4(1H)-one (170 mg, yield: 52%) without further purification. 1H-NMR (CDCl3, 400 MHz) δ 8.09 (d, J=8.0 Hz, 1H), 7.41˜7.44 (m, 1H), 7.29˜7.36 (m, 2H), 7.15˜7.19 (m, 1H), 6.84 (d, J=8.0 Hz, 1H), 6.03 (s, 1H), 5.75 (s, 1H), 5.35 (s, 1H). MS (M+H)+: 278/280.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 h
  3. filtrationfiltered

Sources & evidence

ORD record
ord-b3dbc7f91459428d8bbf3f3ee0a9ab8b
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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