1,4-Dioxane → HCID 57813594, compound

HRID 1941980Notes

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

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

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

Sources & evidence

ORD record: ord-2d45ee4013cf4acca1e15a2b85995a30
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389516B2

Reaction notes

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