Methanol → HCID 178520771, compound

HRID 243361Notes

Reaction equation

C([O:8][CH2:9][CH2:10][C@H:11]([NH:28][C:29]1[N:37]=[CH:36][N:35]=[C:34]2[C:30]=1[N:31]=[CH:32][NH:33]2)[C:12]1[N:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:15]2[CH:23]=[C:24]([F:27])[CH:25]=[CH:26][C:14]=2[N:13]=1)C1C=CC=CC=1.B(Br)(Br)Br.CO>C(Cl)Cl>[F:27][C:24]1[CH:25]=[CH:26][C:14]2[N:13]=[C:12]([C@@H:11]([NH:28][C:29]3[N:37]=[CH:36][N:35]=[C:34]4[C:30]=3[N:31]=[CH:32][NH:33]4)[CH2:10][CH2:9][OH:8])[N:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:15]=2[CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of [(S)-3-benzyloxy-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)propyl]-(9H-purin-6-yl)amine (296 mg, 0.6 mmol) in anhydrous DCM (6 mL) at 0° C. under a nitrogen atmosphere was added dropwise boron tribromide (1.0 M in DCM, 1.2 mL, 1.2 mmol). The reaction mixture was stirred at 0° C. for 1 h. MeOH was then added and the volatiles were removed under reduced pressure. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM) to afford 187 (160 mg, 66%). LCMS (Method K): RT 3.10 min [M+H]+ 404.1 1H NMR (DMSO-d6, 400 MHz): δ 12.55 (1H, s), 8.28-7.83 (3H, m), 7.81-7.44 (6H, m), 7.16-7.01 (1 m), 6.91-6.79 (1H, m), 5.56 (1H, br s), 4.60 (1H, br s), 3.57-3.38 (2H, m), 2.23-2.00 (2H, m). Signals split due to presence of rotamers/tautomers

Workup

customthe volatiles were removed under reduced pressure
customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM)

Sources & evidence

ORD record: ord-7f5737ad287e483f8cb47ceeb85a08c7
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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