Hydrochloric Acid → HCID 178456068, compound

HRID 243442Notes

Reaction equation

HRID 243442 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:31]=[N:32][CH:33]=[C:34]([F:36])[CH:35]=3)[C:7]=2[CH:37]=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[N:17]=[CH:18][NH:19]4)[CH2:12][CH3:13])[N:8]([C:30]3[CH:31]=[N:32][CH:33]=[C:34]([F:36])[CH:35]=3)[C:7]=2[CH:37]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68158161{(S)-1-[6-Fluoro-1-(5-fluoropyridin-3-yl)-1H-benzoimidazol-2-yl]propyl}-[9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine

Product 1

HCID 178456068HCID 178456068, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

HCl (0.25 mL of a 4M solution in dioxane) was added to a solution of {(S)-1-[6-fluoro-1-(5-fluoropyridin-3-yl)-1H-benzoimidazol-2-yl]propyl}-[9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine (96 mg, 0.20 mmol) in MeOH (1 mL) and the reaction mixture stirred at RT for 10 min. The crude 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 359 (76 mg, 94%) as a white solid. LCMS (Method K): RT 3.23 min [M+H]+ 407.1. 1H NMR (CD3OD, 400 MHz): δ 8.59 (1H, s), 8.51 (1H, s), 8.05 (1H, s), 8.03 (1H, br s), 7.95 (1H, d, J=8.4 Hz), 7.65 (1H, dd, J=8.8, 4.6 Hz), 7.07 (1H, ddd, J=9.7, 8.8, 2.6 Hz), 6.88 (1H, dd, J=8.6, 2.6 Hz), 5.54-5.42 (1H, m), 2.26 (1H, dqd, J=14.9, 7.5, 6.4 Hz), 2.12 (1H, dqd, J=14.9, 7.5, 6.4 Hz), 1.01 (3H, t, J=7.5 Hz)

Workup

  1. customThe crude reaction mixture
  2. washeluting with 2M NH3/MeOH
  3. concentrationThe basic fraction was concentrated in vacuo

Sources & evidence

ORD record
ord-a0bd3ca7a02a468fb740883314edabaf
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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