Methanol → HCID 178520772, compound

HRID 243417Notes

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[NH:31][CH:32]=[N:33]2)[C:12]1[N:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N: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:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[C:15]=2[CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of [(S)-3-benzyloxy-1-(6-fluoro-1-pyridin-2-yl-1H-benzoimidazol-2-yl)propyl](7H-purin-6-yl)amine (465 mg, 0.8 mmol) in anhydrous DCM (8 mL) at 0° C. under a nitrogen atmosphere was added dropwise boron tribromide (1.0 M in DCM, 2.4 mL, 2.4 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 0-15% MeOH in DCM) to afford 304 as a white solid (143 mg, 44%). LCMS (Method K): RT 2.73 min [M+H]+ 404.9. 1H NMR (DMSO-d6, 400 MHz): δ 9.56-9.48 (1H, m), 8.65-8.57 (2H, m), 8.49 (1H, s), 8.11 (1H, td, J=7.74, 1.90 Hz), 7.83-7.74 (2H, m), 7.56 (1H, t, J=6.09 Hz), 7.28-7.16 (2H, m), 6.07-5.97 (1H, m), 3.59-3.45 (2H, m), 2.39-2.29 (1H, m), 2.24-2.12 (1H, m)

Workup

customthe volatiles removed under reduced pressure
customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-15% MeOH in DCM)

Sources & evidence

ORD record: ord-661cab8715a7432a9344a068ba632b88
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653089B2

Reaction notes

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