Piperidine → HCID 11429825, compound

HRID 2053421Notes

Reaction equation

HRID 2053421 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[Br:17][C:18]1[CH:19]=[C:20]([CH2:24][C:25](O)=[O:26])[CH:21]=[N:22][CH:23]=1.Cl.CN(C)CCCN=C=NCC.N1CCCCC1>C(Cl)Cl.C1(C)C=CC=CC=1>[Br:17][C:18]1[CH:19]=[C:20]([C:24]2[C:25](=[O:26])[NH:1][C:2]3[C:3]([C:4]=2[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=3)[CH:21]=[N:22][CH:23]=1

Participants

7

Reactant 4

HCID 8082PiperidineHCID 128702-Amino-5-chlorobenzophenoneHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 28025392-(5-Bromopyridin-3-yl)acetic acid

Product 1

HCID 11429825HCID 11429825, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 2-amino-5-chlorobenzophenone (230 mg, 1.00 mmol), 5-bromo-3-pyridineacetic acid (215 mg, 1.00 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (EDCI) (230 mg; 1.20 mmol) in DCM (2.5 mL) was stirred overnight at room temperature. Toluene (2.5 mL) and piperidine (0.2 mL) were then added and the resulting solution was heated to approximately 100° C., allowing the DCM to evaporate from the reaction mixture. After 2 h, the reaction was allowed to cool and stirring was continued at room temperature overnight. The precipitate that formed was filtered and washed with toluene. This crude product was dissolved in chloroform and extracted with water (4×), dried over potassium carbonate (K2CO3) and concentrated to afford the pure quinolinone product (285 mg, 69%). 1H NMR (300 MHz, DMSO-d6) δ 12.4 (br.s, 1H), 8.45 (d, 1H, J=3.0 Hz), 8.21 (d, 1H, J=1.3 Hz), 7.86 (t, 1H, J=1.5 Hz), 7.64 (dd, 1H, J=8.9, 2.3 Hz, 1H), 7.46 (d, 1H, J=8.6 Hz), 7.44-7.31 (m, 3H), 7.28-7.21 (m, 2H), 6.94 (d, 1H, J=2.0 Hz). MS: 413.0 (M+H).

Workup

  1. customto evaporate from the reaction mixture
  2. temperatureto cool
  3. waitwas continued at room temperature overnight
  4. customThe precipitate that formed
  5. filtrationwas filtered
  6. washwashed with toluene
  7. dissolutionThis crude product was dissolved in chloroform
  8. extractionextracted with water (4×)
  9. dry with materialdried over potassium carbonate (K2CO3)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-233fd0228a1e48e8bdf53b28799063d1
Source dataset
uspto-grants-2008_02
Patent number
US07326788B2

Reaction notes

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