Cesium carbonate → HCID 68595618, compound

HRID 410196Notes

Reaction equation

HRID 410196 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]([C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]2[C:30](Br)=[CH:29][CH:28]=[CH:27][N:26]=2)=[CH:20][CH:19]=1)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14].[N:32]1([C:38](=[O:40])[CH3:39])[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:38]([N:32]1[CH2:37][CH2:36][N:35]([C:30]2[C:25]([O:24][C:21]3[CH:22]=[CH:23][C:18]([N:10]([C:2]4[S:1][C:5]5[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=5[N:3]=4)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:19][CH:20]=3)=[N:26][CH:27]=[CH:28][CH:29]=2)[CH2:34][CH2:33]1)(=[O:40])[CH3:39]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 837951-AcetylpiperazineHCID 634876Binap, (A+-)-HCID 59327095HCID 59327095, compound

Product 1

HCID 68595618HCID 68595618, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a round bottomed flask was added tert-butyl benzo[d]thiazol-2-yl(4-(3-bromopyridin-2-yloxy)phenyl)carbamate (0.2713 g, 0.544 mmol), 1-(piperazin-1-yl)ethanone (0.140 g, 1.089 mmol), Pd2(dba)3 (0.050 g, 0.054 mmol), binap (0.068 g, 0.109 mmol), and cesium carbonate (0.174 mL, 2.177 mmol) in toluene to stir at 100° C. overnight. Reaction was allowed to cool to room temperature. Solvent was evaporated. The crude product was purified by reverse-phase preparative HPLC using a Phenomenex Synergi column, 4 micron, MAX-RP, 80 Å, 150×30 MM, 0.1% TFA in ACN/H2O, gradient 10% to 100% over 15 min to provide tert-butyl 4-(3-(4-acetylpiperazin-1-yl)pyridin-2-yloxy)phenyl(benzo[d]thiazol-2-yl)carbamate (MS 545.6). It was taken up in DCM and TFA was added. After purification the title compound was obtained. MS (ESI, pos. ion) m/z: 446.1 (M+1). IC50 (uM) +++++.

Workup

  1. customReaction
  2. temperatureto cool to room temperature
  3. customSolvent was evaporated
  4. customThe crude product was purified by reverse-phase preparative HPLC
  5. customover 15 min

Sources & evidence

ORD record
ord-479ceb7f65554570a1d2cddeb02ed41a
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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