[1-(6-Fluoro-3,4-dihydro-5-oxa-1,2a-diazaacenaphthylen-2-yl)ethyl]-[9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine → HCID 178463557, compound

HRID 243509Notes

Reaction equation

HRID 243509 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:10]2=[C:13]3[C:3]=1[O:4][CH2:5][CH2:6][N:7]3[C:8]([CH:14]([NH:16][C:17]1[N:25]=[CH:24][N:23]=[C:22]3[C:18]=1[N:19]=[CH:20][N:21]3C1CCCCO1)[CH3:15])=[N:9]2>O1CCOCC1.CO>[F:1][C:2]1[CH:12]=[CH:11][C:10]2=[C:13]3[C:3]=1[O:4][CH2:5][CH2:6][N:7]3[C:8]([CH:14]([NH:16][C:17]1[N:25]=[CH:24][N:23]=[C:22]3[C:18]=1[N:19]=[CH:20][NH:21]3)[CH3:15])=[N:9]2

Participants

4

Reactant 1

HCID 68157200[1-(6-Fluoro-3,4-dihydro-5-oxa-1,2a-diazaacenaphthylen-2-yl)ethyl]-[9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine

Product 1

HCID 178463557HCID 178463557, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

Hydrogen chloride, HCl (384 μL of a 4M solution in dioxane) was added to a solution of [1-(6-fluoro-3,4-dihydro-5-oxa-1,2a-diazaacenaphthylen-2-yl)ethyl]-[9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine (130 mg, 0.31 mmol) in MeOH (1 mL) and the reaction was stirred at RT for 20 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 435 (92 mg, 87%) as a pale yellow solid. LCMS (Method K): RT 2.28 min [M+H]+ 340.0. 1H NMR (CD3OD, 400 MHz): δ 8.22 (1H, s), 8.06 (1H, s), 7.06 (1H, dd, J=8.9, 3.1 Hz), 6.91 (1H, dd, J=12.0, 8.9 Hz), 5.78 (1H, br s), 4.63-4.38 (4H, m), 1.79 (3H, d, J=7.0 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-e19fd596e2ff4a32b66c6a8e308d7006
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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