Sodium Carbonate → HCID 1224085, compound

HRID 490193Notes

Reaction equation

HRID 490193 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:28])([F:27])[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:26])[CH2:24]Cl)=[CH:18][CH:17]=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]([CH2:24][C:23]([NH:22][C:19]2[CH:18]=[CH:17][C:16]([O:15][C:14]([F:13])([F:27])[F:28])=[CH:21][CH:20]=2)=[O:26])[CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 944591-(2-Pyridyl)piperazineHCID 6010312-Chloro-N-[4-(trifluoromethoxy)phenyl]acetamide

Product 1

HCID 1224085HCID 1224085, compoundYield 32%

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-trifluoromethoxyphenyl)-2-chloroacetamide (51 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 the residue was purified by preparative HPLC to provide 16 mg (32%) 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), 7.35 (d, J=6 Hz, 2H), 7.55 (t, J=6 Hz, 1H), 7.76 (m, 2H), 8.12 (d, J=5 Hz, 1H), 9.98 (s, 1H); MS (ESI/APCI+) m/e 381 (M+H)+.

Workup

  1. customThe resulting mixture was decanted
  2. concentrationconcentrated
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-8e5dc38eb16a40c7a5d387bf7fc5c4c1
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Reaction notes

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