Boron tribromide → HCID 44218898, compound

HRID 2097586

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([N:10]2[CH2:13][CH:12]([O:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH2:29][O:30]CC5C=CC=CC=5)[CH:22]=4)=[CH:17][N:16]=3)[CH2:11]2)=[O:9])[N:2]=1.B(Br)(Br)Br>ClCCl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([N:10]2[CH2:13][CH:12]([O:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH2:29][OH:30])[CH:22]=4)=[CH:17][N:16]=3)[CH2:11]2)=[O:9])[N:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-{5-[3-(2-Benzyloxy-ethoxy)-phenyl]-pyridin-2-yloxy}-azetidine-1-carboxylic acid pyridazin-3-ylamide (Example 9, 325 mg, 0.65 mmol) was dissolved in anhydrous dichloromethane (10 mL) under a nitrogen atmosphere. The mixture was cooled with an ice water bath and boron tribromide in dichloromethane solution (1M, 0.98 mL, 0.98 mmol) was added drop-wise affording a precipitate. The reaction mixture was stirred at 0° C. for 2 hr. The precipitate was collected by filtration and purified by flash chromatography on silica gel eluting with ethyl acetate, then 5-10% methanol in DCM. Further purification by preparative HPLC at pH4 afforded title compound (13 mg, 5%) as colourless solid.

Workup

temperatureThe mixture was cooled with an ice water bath
customaffording a precipitate
filtrationThe precipitate was collected by filtration
custompurified by flash chromatography on silica gel eluting with ethyl acetate
customFurther purification by preparative HPLC at pH4

Sources & evidence

ORD record: ord-fc450e2c599d47e3aeda39a7b2e0946b
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450346B2

Linked notes

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