Cesium carbonate → HCID 22993392, compound

HRID 1167766Notes

Reaction equation

HRID 1167766 reaction equation
Cl[C:2]1[CH:27]=[CH:26][C:5]([C:6]([NH:8][C:9]2[S:10][C:11]3[C:17]([N:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[CH:16][CH:15]=[C:14]([O:24][CH3:25])[C:12]=3[N:13]=2)=[O:7])=[CH:4][N:3]=1.[C:28]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)(=[O:30])[CH3:29].C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1>[C:28]([N:31]1[CH2:36][CH2:35][N:34]([C:2]2[CH:27]=[CH:26][C:5]([C:6]([NH:8][C:9]3[S:10][C:11]4[C:17]([N:18]5[CH2:23][CH2:22][O:21][CH2:20][CH2:19]5)=[CH:16][CH:15]=[C:14]([O:24][CH3:25])[C:12]=4[N:13]=3)=[O:7])=[CH:4][N:3]=2)[CH2:33][CH2:32]1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 837951-AcetylpiperazineHCID 22993400HCID 22993400, compound

Product 1

HCID 22993392HCID 22993392, compoundYield 31.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

A stirred suspension of 200 mg (0.49 mmol) 6-chloro-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-nicotinamide, 2.53 g (19.8 mmol) 1-acetylpiperazine and 290 mg (0.89 mmol) cesium carbonate in 4 ml NMP in a thick-walled glass pressure tube fitted with a teflon cap was heated at 120° C. for 24 h. The reaction mixture was then cooled to room temperature and poured onto water. The mixture was extracted three times with dichloromethane, and the combined organic phases were washed with saturated brine, dried over sodium sulfate, and concentrated in vacuo. Flash chromatography (0/99-4/96 methanol/dichlormoethane) followed by trituration in ether afforded 77 mg (31%) 6-(4-acetyl-piperazin-1-yl)-N-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-nicotinamide as a white crystalline solid. ES-MS m/e (%): 519 (M+Na+, 26), 417 (M+H+, 100).

Workup

  1. customcap
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. additionpoured onto water
  4. extractionThe mixture was extracted three times with dichloromethane
  5. washthe combined organic phases were washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3387d160083a405e89b457e2187604cf
Source dataset
uspto-grants-2003_09
Patent number
US06620811B2

Reaction notes

Loading…