Hydrochloric Acid → HCID 178461924, compound

HRID 243510Notes

Reaction equation

HRID 243510 reaction equation
Cl.[F:2][C:3]1[CH:13]=[CH:12][C:11]2=[C:14]3[C:4]=1[O:5][CH2:6][C@@H:7]([CH3:33])[N:8]3[C:9]([C@@H:15]([NH:17][C:18]1[N:26]=[CH:25][N:24]=[C:23]3[C:19]=1[N:20]=[CH:21][N:22]3C1CCCCO1)[CH3:16])=[N:10]2>O1CCOCC1.CO>[F:2][C:3]1[CH:13]=[CH:12][C:11]2=[C:14]3[C:4]=1[O:5][CH2:6][C@@H:7]([CH3:33])[N:8]3[C:9]([C@@H:15]([NH:17][C:18]1[N:26]=[CH:25][N:24]=[C:23]3[C:19]=1[N:20]=[CH:21][NH:22]3)[CH3:16])=[N:10]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68158131HCID 68158131, compound

Product 1

HCID 178461924HCID 178461924, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

HCl (260 μL of a 4M solution in dioxane) was added to a solution of [(S)-1-((R)-6-fluoro-3-methyl-3,4-dihydro-5-oxa-1,2a-diazaacenaphthylen-2-yl)ethyl][9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine (93 mg, 0.21 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 439 (71 mg, 96%) as a white solid. LCMS (Method K): RT 2.50 min [M+H]+ 354.0. 1H NMR (CD3OD, 400 MHz): δ 8.21 (1H, s), 8.07 (1H, s), 7.07 (1H, dd, J=8.8, 3.1 Hz), 6.93 (1H, dd, J=11.9, 8.8 Hz), 5.89 (1H, br s), 4.88 (1H, qdd, J=6.6, 2.3, 1.6 Hz), 4.45 (1H, dd, J=11.8, 1.6 Hz), 4.22 (1H, dd, J=11.8, 2.3 Hz), 1.76 (3H, d, J=7.0 Hz), 1.44 (3H, d, J=6.6 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-f440827c8eec4251847a635a23f4172a
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

Loading…