Hydrochloric Acid → (S)-N-(1-(6-fluoro-1-phenyl-1H-benzo[d]imidazol-2-yl)propyl)-7H-purin-6-amine

HRID 243443Notes

Reaction equation

HRID 243443 reaction equation
Cl.[F:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([C@@H:11]([NH:14][C:15]3[N:23]=[CH:22][N:21]=[C:20]4[C:16]=3[N:17]=[CH:18][N:19]4C3CCCCO3)[CH2:12][CH3:13])[N:8]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:7]=2[CH:36]=1>O1CCOCC1.CO>[F:2][C:3]1[CH:4]=[CH:5][C:6]2[N:10]=[C:9]([C@@H:11]([NH:14][C:15]3[N:23]=[CH:22][N:21]=[C:20]4[C:16]=3[NH:17][CH:18]=[N:19]4)[CH2:12][CH3:13])[N:8]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:7]=2[CH:36]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68157227[(S)-1-(6-Fluoro-1-phenyl-1H-benzoimidazol-2-yl)propyl]-[9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine

Product 1

HCID 60161900(S)-N-(1-(6-fluoro-1-phenyl-1H-benzo[d]imidazol-2-yl)propyl)-7H-purin-6-amineYield 98.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

HCl (0.22 mL of a 4M solution in dioxane) was added to a solution of [(S)-1-(6-fluoro-1-phenyl-1H-benzoimidazol-2-yl)propyl]-[9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine (82 mg, 0.17 mmol) in MeOH (2 mL) and the reaction was stirred at RT for 10 min. The reaction mixture was passed through a 2 g Isolute® SCX-2 cartridge, eluting with 2M NH3/MeOH. The basic fraction was concentrated in vacuo to give 360 (65 mg, quant.) as a white solid. LCMS (Method K): RT 3.58 min [M+H]+ 388.1. 1H NMR (CD3OD, 400 MHz): δ 8.06 (1H, s), 8.04 (1H, br s), 7.61 (1H, dd, J=8.8, 4.6 Hz), 7.57-7.43 (5H, m), 7.02 (1H, ddd, J=9.6, 8.8, 2.7 Hz), 6.76 (1H, dd, J=8.7, 2.7 Hz), 5.44 (1H, br s), 2.14 (1H, dqd, J=14.8, 7.4, 6.5 Hz), 2.05 (1H, dqd, J=14.8, 7.4, 6.5 Hz), 0.95 (3H, t, J=7.4 Hz)

Workup

  1. washeluting with 2M NH3/MeOH
  2. concentrationThe basic fraction was concentrated in vacuo

Sources & evidence

ORD record
ord-e0f1ea1e1b4c4638a99a02e010df62f9
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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