Sodium Carbonate → Ammonia

HRID 2196189Notes

Reaction equation

HRID 2196189 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:14][C:15]([C:17]2[C:18]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:16])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.Br[CH:30]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:31]([N:33]([CH2:36][CH3:37])[CH2:34][CH3:35])=[O:32].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CCOC(C)=O>[NH3:8].[CH2:36]([N:33]([CH2:34][CH3:35])[C:31]([CH:30]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[N:11]1[CH2:12][CH2:13][N:8]([C:7]2[CH:6]=[CH:5][C:4]([NH:14][C:15]([C:17]3[C:18]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:19][CH:20]=[CH:21][CH:22]=3)=[O:16])=[CH:3][C:2]=2[F:1])[CH2:9][CH2:10]1)=[O:32])[CH3:37]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 14897375HCID 14897375, compoundHCID 66931694HCID 66931694, compound

Product 2

HCID 222AmmoniaHCID 56670260HCID 56670260, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of biphenyl-2-carboxylic acid (3-fluoro-4-piperazin-1-yl-phenyl)-amide (0.030 g, 0.08 mmol), 2-bromo-N,N-diethyl-2-phenyl-acetamide (0.025 g, 0.09 mmol), and Na2CO3 (0.013 g, 0.1 mmol) in DMF (2 mL) was stirred at room temperature. After 18 h, the reaction mixture was diluted with EtOAc (25 mL) and washed with H2O (3×15 mL). The organic layers were combined, dried (Na2SO4), and concentrated. Chromatography of the resulting residue (SiO2: 2 M NH3 in MeOH/CH2Cl2) yielded the title compound.

Workup

  1. washwashed with H2O (3×15 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4a099b9f3ae64f59934196a085765057
Source dataset
uspto-grants-2012_12
Patent number
US08338426B2

Reaction notes

Loading…