Sodium Carbonate → HCID 16667040, compound

HRID 1927591Notes

Reaction equation

HRID 1927591 reaction equation
[CH2:1]([CH:3]([CH2:20][CH3:21])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[C:9]([F:19])[CH:8]=1)=[O:5])[CH3:2].C([O-])([O-])=O.[Na+].[Na+].Br[CH:29]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:30]([N:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1)=[O:31]>CN(C=O)C.CCOC(C)=O>[NH3:6].[CH2:20]([CH:3]([CH2:1][CH3:2])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:14][CH2:15][N:16]([CH:29]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:30](=[O:31])[N:32]3[CH2:33][CH2:34][CH2:35][CH2:36]3)[CH2:17][CH2:18]2)=[C:9]([F:19])[CH:8]=1)=[O:5])[CH3:21]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 54155058HCID 54155058, compoundHCID 58870794HCID 58870794, compound

Product 2

HCID 222AmmoniaHCID 16667040HCID 16667040, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-ethyl-N-(3-fluoro-4-piperazin-1-yl-phenyl)-butyramide (0.08 g, 0.27 mmol) and Na2CO3 (0.03 g, 0.30 mmol) in DMF (2 mL) was added 2-bromo-2-phenyl-1-pyrrolidin-1-yl-ethanone (0.09 g, 0.30 mmol). After 18 h of stirring the mixture was diluted with EtOAc (30 mL) and washed with water (3×30 mL). The organic layer was dried (MgSO4) and concentrated. Chromatography of the resulting residue (SiO2; 2 M NH3 in MeOH/DCM) gave the title compound (0.08 mg, 51%). MS (ESI): mass calcd. for C28H37FN4O2, 480.29. m/z found, 481.4 [M+H]+. 1H NMR (DMSO): 7.52-7.47 (m, 3H), 7.36-7.29 (m, 3H), 7.07-7.05 (m, 1H), 6.87-6.83 (m, 1H), 3.42-3.38 (m, 1H), 3.09 (br s, 4H), 2.69 (s, 4H), 2.10-1.45 (m, 12H), 0.96-0.94 (m, 6H).

Workup

  1. washwashed with water (3×30 mL)
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-d3e690336664486a9979cdca58def507
Source dataset
uspto-grants-2012_05
Patent number
US08183239B2

Reaction notes

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