Sodium Carbonate → HCID 4818551, compound

HRID 490198Notes

Reaction equation

HRID 490198 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[F:13][C:14]([F:27])([F:26])[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:25])[CH2:23]Cl)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]1[CH2:8][CH2:9][N:10]([CH2:23][C:22]([NH:21][C:18]2[CH:19]=[CH:20][C:15]([C:14]([F:13])([F:26])[F:27])=[CH:16][CH:17]=2)=[O:25])[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 944591-(2-Pyridyl)piperazineHCID 27364642-chloro-N-[4-(trifluoromethyl)phenyl]acetamide

Product 1

HCID 4818551HCID 4818551, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

A mixture of 1-pyridin-2-ylpiperazine (24 mg, 0.15 mmol, Aldrich), N-(4-trifluoromethylphenyl)-2-chloroacetamide (48 mg, 0.20 mmol, Maybridge) and sodium carbonate (50 mg) in N,N-dimethylformamide/water (2:1, 2 mL) was shaken at room temperature for 18 hours. The resulting mixture was decanted, concentrated under reduced pressure and the residue purified by preparative HPLC to provide 20 mg (37%) of the desired product. 1H NMR (500 MHz, DMSO-d6) δ 2.60 (t, J=4 Hz, 4H), 3.21 (s, 2H), 3.58 (t, J=4 Hz, 4H), 6.63 (t, J=5 Hz, 1H), 6.83 (d, J=6 Hz, 1H), 7.30 (m, 1H), 7.55 (m, 2H), 7.80 (m, 2H), 8.12 (d, J=5 Hz, 1H), 10.08 (s, 1H); MS (ESI/APCI+) m/e 365 (M+H)+.

Workup

  1. customThe resulting mixture was decanted
  2. concentrationconcentrated under reduced pressure
  3. customthe residue purified by preparative HPLC

Sources & evidence

ORD record
ord-69d159a25ccb4a4b98dcd72f5a1abe7d
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Reaction notes

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