1,4-Dioxane → HCID 57813594, compound

HRID 1010689Notes

Reaction equation

HRID 1010689 reaction equation
[CH2:1]([NH:3][C:4](=[O:30])[NH:5][C:6]1[S:7][C:8]2[C:14]([C:15]3[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]=3)=[CH:13][C:12](OS(C(F)(F)F)(=O)=O)=[CH:11][C:9]=2[N:10]=1)[CH3:2].[N:31]1[CH:36]=[CH:35][CH:34]=[C:33](B(O)O)[CH:32]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O1CCOCC1>CO>[CH2:1]([NH:3][C:4]([NH:5][C:6]1[S:7][C:8]2[C:14]([C:15]3[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][N:16]=3)=[CH:13][C:12]([C:33]3[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=3)=[CH:11][C:9]=2[N:10]=1)=[O:30])[CH3:2]

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 27343783-Pyridinylboronic acidHCID 58033209HCID 58033209, compound

Product 1

HCID 57813594HCID 57813594, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A stirred mixture of the crude Trifluoro-methanesulfonic acid 2-(3-ethyl-ureido)-7-(4-methyl-pyridin-2-yl)-benzothiazol-5-yl ester (44 mg, 0.096 mmol), 3-pyridineboronic acid (13 mg, 0.106 mmol), powdered potassium phosphate tribasic (25 mg, 0.115 mmol), anhydrous 1,4-dioxane (0.7 ml) and anhydrous methanol (1.2 ml) was purged with nitrogen for 15 min. 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride complex (12 mg, 0.0144 mmol) was added and the mixture heated at 80° C. for 16 h under an atmosphere of nitrogen. After cooling to ambient temperature, the mixture was filtered through celite and washed through with methanol. The filtrate was evaporated in vacuo to give the crude 1-Ethyl-3-[7-(4-methyl-pyridin-2-yl)-5-pyridin-3-yl-benzothiazol-2-yl]-urea.

Workup

  1. customwas purged with nitrogen for 15 min
  2. addition1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride complex (12 mg, 0.0144 mmol) was added
  3. temperatureAfter cooling to ambient temperature
  4. filtrationthe mixture was filtered through celite
  5. washwashed through with methanol
  6. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-7ccde41944154fe9a5b611d069c5a6f1
Source dataset
uspto-grants-2011_07
Patent number
US07977340B2

Reaction notes

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