Boron tribromide → HCID 178465303, compound

HRID 447045Notes

Reaction equation

[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]3[N:17]=[C:18]([O:21]C)[S:19][CH:20]=3)=[CH:14][C:13]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].B(Br)(Br)Br>C(Cl)Cl>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]3[N:17]=[C:18]([OH:21])[S:19][CH:20]=3)=[CH:14][C:13]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 1-ethyl-3-[7-(2-methoxy-thiazol-4-yl)-5-pyridin-3-yl-benzothiazol-2-yl]-urea (0.05 g, 0.12 mmol) in dry DCM (5 mL) was added BBr3 (0.20 mL) under nitrogen atmosphere at 0° C. The reaction mixture was then heated at 50° C. for 24 h under nitrogen atmosphere. After the completion of the reaction (TLC monitoring), the reaction mixture was cooled to 0° C. and then quenched with ice-cold water followed by extraction with DCM. The combined organic layers were dried over anhydrous Na2SO4, and evaporated to dryness under reduced pressure. The crude residue was purified over silica gel (230-400 M) using DCM-MeOH (96:4) to provide the title compound as light greenish solid (3.5 mg, 7%).

Workup

customAfter the completion of the reaction (TLC monitoring)
temperaturethe reaction mixture was cooled to 0° C.
customquenched with ice-cold water
extractionfollowed by extraction with DCM
dry with materialThe combined organic layers were dried over anhydrous Na2SO4
customevaporated to dryness under reduced pressure
customThe crude residue was purified over silica gel (230-400 M)

Sources & evidence

ORD record: ord-dbf1983a15a64bc89081b07167db8b47
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481544B2

Reaction notes

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