hydrochloric acid HCl → HCID 178461923, compound

HRID 243512Notes

Reaction equation

HRID 243512 reaction equation
Cl.Cl.[F:3][C:4]1[CH:14]=[CH:13][C:12]2=[C:15]3[C:5]=1[O:6][CH2:7][C@H:8]([CH3:34])[N:9]3[C:10]([C@@H:16]([NH:18][C:19]1[N:27]=[CH:26][N:25]=[C:24]3[C:20]=1[N:21]=[CH:22][N:23]3C1CCCCO1)[CH3:17])=[N:11]2>O1CCOCC1.CO>[F:3][C:4]1[CH:14]=[CH:13][C:12]2=[C:15]3[C:5]=1[O:6][CH2:7][C@H:8]([CH3:34])[N:9]3[C:10]([C@@H:16]([NH:18][C:19]1[N:27]=[CH:26][N:25]=[C:24]3[C:20]=1[N:21]=[CH:22][NH:23]3)[CH3:17])=[N:11]2

Participants

5

Reactant 2

HCID 21225539hydrochloric acid HClHCID 68157045HCID 68157045, compound

Product 1

HCID 178461923HCID 178461923, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Hydrogen chloride HCl (340 μL of a 4M solution in dioxane) was added to a solution of [(S)-1-((S)-6-fluoro-3-methyl-3,4-dihydro-5-oxa-1,2a-diazaacenaphthylen-2-yl)ethyl][9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine (117 mg, 0.27 mmol) in MeOH (1 mL) and the reaction was stirred at RT for 30 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 441 (88 mg, 92%) as an off-white solid. LCMS (Method K): RT 2.61 min [M+H]+ 354.0. 1H NMR (CD3OD, 400 MHz): δ 8.23 (1H, s), 8.05 (1H, s), 7.08 (1H, dd, J=8.8, 3.1 Hz), 6.93 (1H, dd, J=12.1, 8.8 Hz), 5.77 (1H, br s), 5.19 (1H, qdd, J=6.7, 2.6, 1.8 Hz), 4.48 (1H, dd, J=11.5, 1.8 Hz), 4.20 (1H, dd, J=11.5, 2.6 Hz), 1.80 (3H, d, J=7.0 Hz), 1.47 (3H, d, J=6.7 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-3c52abdd40e34147a3b12ab89f12a64b
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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