Cesium carbonate → HCID 85470480, compound

HRID 1403729Notes

Reaction equation

HRID 1403729 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[S:10]2(=[O:23])=[O:22])=[C:4]([F:24])[CH:3]=1.[N:25]1([C:31](=[O:33])[CH3:32])[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:31]([N:25]1[CH2:30][CH2:29][N:28]([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][N:9]3[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[S:10]3(=[O:23])=[O:22])=[C:4]([F:24])[CH:3]=2)[CH2:27][CH2:26]1)(=[O:33])[CH3:32]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 837951-AcetylpiperazineHCID 90409510HCID 90409510, compound

Product 1

HCID 85470480HCID 85470480, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-[(4-bromo-2-fluorophenyl)methyl]-7-phenyl-1λ6,2,7-thiadiazepane-1,1-dione (200 mg, 0.48 mmol), 1-(piperazin-1-yl)ethanone (93 mg, 0.72 mmol), Pd2(dba)3 (44 mg, 0.048 mmol), Xant-phos (55 mg, 0.096 mmol), and Cs2CO3 (469 mg, 1.44 mmol) in 1,4-dioxane (10 mL) under nitrogen atmosphere was stirred at 100° C. for 16 hours. The reaction mixture was filtered and concentrated under reduced pressure. The crude product was purified by preparative HPLC to afford 2-{[4-(4-Acetylpiperazin-1-yl)-2-fluorophenyl]methyl}-7-phenyl-1λ6,2,7-thiadiaze-pane-1,1-dione as brown oil (68 mg, 31%). 1H NMR (500 MHz, CDCl3) δ ppm 7.35-7.40 (m, 6H), 6.67-6.69 (m, 1H), 6.55-6.58 (m, 1H), 4.50 (s, 2H), 3.76 (t, J=5.5, 2H), 3.60-3.65 (m, 4H), 3.36 (t, J=5.5, 2H), 3.16-3.21 (m, 4H), 2.14 (s, 3H), 1.98 (t, J=5, 2H), 1.90 (t, J=3.5, 2H); LCMS (ESI): m/z=234.9 [M-2-phenyl-1λ6,2,7-thiadiazepane-1,1-dione+H]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-5df40ac49cf84760868e0caf4f7f1891
Source dataset
uspto-grants-2014_12
Patent number
US08912219B2

Reaction notes

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