Methanol → HCID 178521075, compound

HRID 243406Notes

Reaction equation

C([O:8][CH2:9][C@H:10]([NH:27][C:28]1[N:36]=[CH:35][N:34]=[C:33]2[C:29]=1[NH:30][CH:31]=[N:32]2)[C:11]1[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[C:14]2[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:13]=2[N:12]=1)C1C=CC=CC=1.B(Br)(Br)Br.CO>C(Cl)Cl>[F:26][C:23]1[CH:24]=[CH:25][C:13]2[N:12]=[C:11]([C@@H:10]([NH:27][C:28]3[N:36]=[CH:35][N:34]=[C:33]4[C:29]=3[N:30]=[CH:31][NH:32]4)[CH2:9][OH:8])[N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[C:14]=2[CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of [(R)-2-benzyloxy-1-(6-fluoro-1-pyridin-2-yl-1H-benzoimidazol-2-yl)ethyl](7H-purin-6-yl)amine (336 mg, 0.7 mmol) in anhydrous DCM (8 mL) at 0° C. under a nitrogen atmosphere was added dropwise boron tribromide (1.0M in DCM, 2.6 mL, 2.6 mmol). The reaction mixture was stirred at 0° C. for 1 h. MeOH was added and the volatiles removed under reduced pressure. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) to afford 280 as a white solid (225 mg, 82%). LCMS (Method K): RT 2.72 min [M+H]+ 391.0. 1H NMR (DMSO-d6, 400 MHz): δ 12.90 (1H, br s), 8.68 (1H, s), 8.20-8.08 (2H, m), 8.03 (1H, s), 7.85 (1H, d, J=7.87 Hz), 7.71 (1H, dd, J=8.80, 4.89 Hz), 7.57 (1H, t, J=6.07 Hz), 7.30-7.06 (3H, m), 5.84 (1H, s), 5.11 (1H, s), 4.01-3.82 (2H, m)

Workup

customthe volatiles removed under reduced pressure
customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM)

Sources & evidence

ORD record: ord-8da43708a5754f66b22edd18c7072ed6
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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