HCID 68157574, compound → HCID 178461899, compound

HRID 243412Notes

Reaction equation

HRID 243412 reaction equation
[Br:1][C:2]1[C:7]2[N:8]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:9]([C@@H:11]([NH:13][C:14]3[N:22]=[CH:21][N:20]=[C:19]4[C:15]=3[N:16]=[CH:17][N:18]4C3CCCCO3)[CH3:12])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1>Cl>[Br:1][C:2]1[C:7]2[N:8]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:9]([C@@H:11]([NH:13][C:14]3[N:22]=[CH:21][N:20]=[C:19]4[C:15]=3[N:16]=[CH:17][NH:18]4)[CH3:12])=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 68157574HCID 68157574, compound

Product 1

HCID 178461899HCID 178461899, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

[(S)-1-(7-Bromo-1-phenyl-1H-benzoimidazol-2-yl)ethyl][9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine (60 mg, 0.12 mmol) was dissolved in HCl (1 mL, 1M in MeOH) and the resulting solution was stirred for 15 min. The solvent was removed in vacuo and the residue was crystallised from hot IPA to give 292 as white crystals (53 mg, 98%). 1H NMR (DMSO-d6, 400 MHz): δ 8.64-8.47 (2H, m), 7.82-7.76 (2H, m), 7.74-7.50 (5H, m), 7.44 (1H, t, J=8.1 Hz), 5.53-5.41 (1H, m), 1.84 (3H, d, J=7.0 Hz). LCMS (Method K): RT 3.69 min; m/z [M+H]+ 434/436

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was crystallised from hot IPA

Sources & evidence

ORD record
ord-1a7f3cd0f5af4635b4b0c1a26ba24845
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…