Cesium carbonate → HCID 46214714, compound

HRID 410249Notes

Reaction equation

HRID 410249 reaction equation
F[C:2]1[C:7]([CH:8]2[CH2:14][CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[S:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[NH:24][C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1.O.CO>[O:11]1[CH2:12][CH2:13][CH2:14][CH:8]([C:7]2[C:2]([O:31][C:28]3[CH:27]=[CH:26][C:25]([NH:24][C:16]4[S:15][C:19]5[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=5[N:17]=4)=[CH:30][CH:29]=3)=[N:3][CH:4]=[CH:5][CH:6]=2)[CH2:9][CH2:10]1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 593268134-(Benzo[d]thiazol-2-ylamino)phenolHCID 59327121HCID 59327121, compound

Product 1

HCID 46214714HCID 46214714, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

2-Fluoro-3-(oxepan-4-yl)pyridine (0.055 g, 0.28 mmol), 4-(benzo[d]thiazol-2-ylamino)phenol (0.20 g, 0.85 mmol), and cesium carbonate (0.28 mL, 0.85 mmol) were mixed in NMP (0.75 mL). The reaction mixture was placed under a nitrogen atmosphere and stirred at 120° C. for 17 h. The reaction mixture was cooled to room temperature, diluted with water, and extracted with EtOAc (2×). The combined organic layers were washed with 1 M aqueous sodium hydroxide, washed with sat. sodium chloride, dried over magnesium sulfate, and concentrated in vacuo. The resulting crude product was purified by silica gel chromatography to yield an orange solid. The solid was slurried in MeOH and filtered to give N-(4-(3-(oxepan-4-yl)pyridin-2-yloxy)phenyl)benzo[d]thiazol-2-amine. MS (ESI, pos. ion) m/z: 418.1 (M+1). IC50 (uM) +++++.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organic layers were washed with 1 M aqueous sodium hydroxide
  4. washwashed with sat. sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude product was purified by silica gel chromatography
  8. customto yield an orange solid
  9. filtrationfiltered

Sources & evidence

ORD record
ord-df2e7e27ea1b49eb9dd1b65fc9d564ee
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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