Hydrochloric Acid → Gsk-2245035

HRID 2367967Notes

Reaction equation

HRID 2367967 reaction equation
Cl.[CH3:2][C@H:3]([O:7][C:8]1[N:16]=[C:15]2[C:11]([N:12]=[C:13]([O:28]C)[N:14]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[C:10]([NH2:30])[N:9]=1)[CH2:4][CH2:5][CH3:6]>O1CCOCC1.CO>[NH2:30][C:10]1[N:9]=[C:8]([O:7][C@@H:3]([CH3:2])[CH2:4][CH2:5][CH3:6])[N:16]=[C:15]2[C:11]=1[NH:12][C:13](=[O:28])[N:14]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 592525742-{[(1S)-1-Methylbutyl]oxy}-8-(methyloxy)-9-[5-(1-piperidinyl)pentyl]-9H-purin-6-amine2×

Product 1

HCID 44623937Gsk-2245035Yield 83.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 312751,4-DioxaneSolvent

Procedure

A solution of hydrogen chloride in dioxane (4M, 0.71 mL) was added to a solution of 2-{[(1S)-1-methylbutyl]oxy}-8-(methyloxy)-9-[5-(1-piperidinyl)pentyl]-9H-purin-6-amine (for example, as prepared for Intermediate 9) (0.046 g, 0.126 mmol) in methanol (3 mL). The resultant mixture was allowed to stand overnight at room temperature and then blown down under nitrogen. The residue was dissolved in methanol and loaded onto a 2 g aminopropyl SPE cartridge (pre-conditioned with methanol), eluted with methanol and the resultant solution blown down under nitrogen to give the title compound as a yellow solid (40.97 mg).

Workup

  1. washeluted with methanol

Sources & evidence

ORD record
ord-f9fe5cc21ec540ac9a32bda322aa0589
Source dataset
uspto-grants-2014_04
Patent number
US08703754B2

Reaction notes

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