Boron tribromide → HCID 178461938, compound

HRID 243465Notes

Reaction equation

C([O:8][C@@H:9]1[CH2:12][C@H:11]([N:13]2[C:17]3[CH:18]=[C:19]([F:22])[CH:20]=[CH:21][C:16]=3[N:15]=[C:14]2[C@@H:23]([NH:25][C:26]2[N:34]=[CH:33][N:32]=[C:31]3[C:27]=2[N:28]=[CH:29][NH:30]3)[CH3:24])[CH2:10]1)C1C=CC=CC=1.B(Br)(Br)Br>C(Cl)Cl>[F:22][C:19]1[CH:20]=[CH:21][C:16]2[N:15]=[C:14]([C@@H:23]([NH:25][C:26]3[N:34]=[CH:33][N:32]=[C:31]4[C:27]=3[N:28]=[CH:29][NH:30]4)[CH3:24])[N:13]([CH:11]3[CH2:12][CH:9]([OH:8])[CH2:10]3)[C:17]=2[CH:18]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of [(S)-1-[1-(cis-3-benzyloxycyclobutyl)-6-fluoro-1H-benzoimidazol-2-yl]ethyl]-(9H-purin-6-yl)amine (0.12 g, 0.26 mmol) in DCM (5 mL) cooled to 0° C. To this mixture was added boron tribromide (1M in DCM, 0.53 mL, 0.53 mmol) dropwise and the resultant mixture stirred at RT for 2 h. The reaction mixture was quenched with MeOH (2 mL) and concentrated in vacuo. The resulting yellow was solid purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) to afford 391 as an off-white glassy solid (50 mg, 50%). LCMS (Method K): RT 2.21 min [M+H]+ 368.3. 1H NMR (DMSO-d6): δ 12.8 (1H, br s), 8.21 (1H, s), 8.09 (1H, s), 7.78-7.89 (1H, m), 7.47-7.61 (2H, m), 6.95-7.04 (1H, m), 5.78 (1H, br s), 5.43 (1H, qn, J=8.82 Hz), 5.11 1H, d, J=4.2 Hz), 4.41-4.50 (1H, m), 2.86-3.04 (2H, m), 2.26-2.38 (1H, m), 2.08-2.20 (1H, m), 1.59 (1H, d, J=6.7 Hz)

Workup

customThe reaction mixture was quenched with MeOH (2 mL)
concentrationconcentrated in vacuo
custompurified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM)

Sources & evidence

ORD record: ord-65ab5c600da147d0811f1ad1289cde05
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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