p-Toluenesulfonic acid → HCID 136927183, compound

HRID 2201552Notes

Reaction equation

HRID 2201552 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][C:8]([Br:11])=[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.OS([O-])=O.[Na+].CC1C=CC(S(O)(=O)=O)=CC=1>CC(N(C)C)=O>[Br:11][C:8]1[CH:9]=[N:10][C:2]2[N:1]=[C:16]([C:15]3[CH:18]=[CH:19][CH:20]=[C:13]([F:12])[CH:14]=3)[NH:6][C:4](=[O:5])[C:3]=2[CH:7]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 680093-FluorobenzaldehydeHCID 23665763Sodium Bisulfite3×HCID 529879382-Amino-5-bromopyridine-3-carboxamide

Product 1

HCID 136927183HCID 136927183, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of 2-amino-5-bromonicotinamide (100 mg, 0.46 mmol), 3-fluorobenzaldehyde (69 mg, 0.56 mmol), NaHSO3 (40 mg, 0.38 mmol), 4-methylbenzene sulfonic acid (15 mg, 0.05 mmol) in DMAc (3 mL) was stirred at 115° C. for 1.5 h, then additional NaHSO3 (40 mg, 0.38 mmol) was added to the mixture. After 1.5 h, the third portion of NaHSO3 (40 mg, 0.38 mmol) was added to the mixture. After being stirred overnight at 115° C., the reaction mixture was concentrated in vacuo, suspended in water and filtered to give the product of 6-bromo-2-(3-fluorophenyl)pyrido[2,3-d]pyrimidin-4(3H)-one (70 mg, yield: 47%), which was used for the next step without further purification. 1H-NMR (DMSO-d6, 400 MHz) δ 13.04 (br s, 1H), 9.07 (d, J=2.8 Hz, 1H), 8.65 (d, J=2.8 Hz, 1H), 8.08 (d, J=8.0 Hz, 1H), 8.02 (dd, J=9.6, 1.6 Hz, 1H), 7.60˜7.68 (m, 1H), 7.45˜7.54 (m, 1H). MS (M+H)+: 320/322.

Workup

  1. waitAfter 1.5 h
  2. stirringAfter being stirred overnight at 115° C.
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. filtrationfiltered

Sources & evidence

ORD record
ord-8e7d4ac5008e4e018b6ce8ea5354aab6
Source dataset
uspto-grants-2016_06
Patent number
US09364482B2

Reaction notes

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