Boron tribromide → HCID 178461938, compound

HRID 243464Notes

Reaction equation

HRID 243464 reaction equation
C([O:8][CH:9]1[CH2:12][CH: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

4

Reactant 2

HCID 25134Boron tribromideHCID 178461939HCID 178461939, compound

Product 1

HCID 178461938HCID 178461938, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of [(S)-1-[1-(3-benzyloxycyclobutyl)-6-fluoro-1H-benzoimidazol-2-yl]ethyl]-(9H-purin-6-yl)amine (0.13 g, 0.29 mmol) in DCM (5 mL) was cooled to 0° C. To this mixture was added boron tribromide (2.1 mL, 1.43 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 solid was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM) to afford 390 as an off-white glassy solid (50 mg, 50%). 1H NMR (DMSO-d6): δ 8.98 (1H, s), 8.55-8.37 (2H, m), 7.93 (1H, d, J=9.74 Hz), 7.69 (1H, dd, J=8.92, 4.99 Hz), 7.21 (1H, t, J=9.90 Hz), 5.89 (1H, s), 4.86-4.75 (1H, m), 4.05-3.95 (1H, m), 2.97-2.62 (4H, m), 1.70 (3H, d, J=6.75 Hz)

Workup

  1. customThe reaction mixture was quenched with MeOH (2 mL)
  2. concentrationconcentrated in vacuo
  3. customThe resulting yellow solid was purified by column chromatography (Si—PCC, gradient 0-10% MeOH in DCM)

Sources & evidence

ORD record
ord-0fb2269a697a49b9ac17c656d96a1cfa
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…