Hydrochloric Acid → HCID 178461929, compound

HRID 243294Notes

Reaction equation

HRID 243294 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C@@H:10]([NH:12][C:13]3[N:21]=[CH:20][N:19]=[C:18]4[C:14]=3[N:15]=[CH:16][N:17]4C3CCCCO3)[CH3:11])[N:7]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:6]=2[CH:34]=1.Cl>CCOC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C@@H:10]([NH:12][C:13]3[N:21]=[CH:20][N:19]=[C:18]4[C:14]=3[N:15]=[CH:16][NH:17]4)[CH3:11])[N:7]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:6]=2[CH:34]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68157440[(S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]-[9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine

Product 1

HCID 178461929HCID 178461929, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Alternatively, [(S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)ethyl]-[9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine (30 g, 65.6 mmol) was dissolved in EtOAc (200 mL) and HCl (1 M in MeOH, 210 mL) was added dropwise and the resulting solution was stirred for 2 h. The solvents were removed in vacuo and the resulting solid was recrystallised from hot EtOAc/EtOH to give 123 as a white crystalline solid (11 g, 45%). Further product crystallised from the mother liquors. 1H NMR (MeOD-d4, 400 MHz): δ 8.60 (1H, s), 8.53 (1H, s), 7.8 (1H, dd, J 9.8, 4.2 Hz), 7.67 (5H, br s), 7.42 (1H, td, J 9.2, 2.3 Hz), 7.14 (1H, dd, J 7.1, 2.4 Hz), 5.67 (1H, m), 1.87 (3H, d, J=6.9 Hz)

Workup

  1. customThe solvents were removed in vacuo
  2. customthe resulting solid was recrystallised from hot EtOAc/EtOH

Sources & evidence

ORD record
ord-1833d8bea37b4a2fb4573c83dc01f183
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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