Hydrochloric Acid → HCID 178495893, compound

HRID 243364Notes

Reaction equation

HRID 243364 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([C@@H:10]([NH:14][C:15]3[N:23]=[CH:22][N:21]=[C:20]4[C:16]=3[N:17]=[CH:18][N:19]4C3CCCCO3)[CH2:11][O:12][CH3:13])[N:7]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:6]=2[C:36]=1[F:37].Cl>CO.O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH:10]([NH:14][C:15]3[N:23]=[CH:22][N:21]=[C:20]4[C:16]=3[N:17]=[CH:18][NH:19]4)[CH2:11][O:12][CH3:13])[N:7]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:6]=2[C:36]=1[F:37]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68157695HCID 68157695, compound

Product 1

HCID 178495893HCID 178495893, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of [(R)-1-(6,7-difluoro-1-phenyl-1H-benzoimidazol-2-yl)-2-methoxyethyl]-[9-(tetrahydro-pyran-2-yl)-9H-purin-6-yl]amine (290 mg, 0.57 mmol) in methanol (5 mL) was added HCl in dioxane (0.5 mL, 4M) and the reaction stirred at RT for 30 min. The reaction mixture was concentrated in vacuo and the resultant residue dissolved in EtOAc (10 mL). The solution was washed with sat. aq. NaHCO3 and the product extracted with EtOAc (3×10 mL). The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The resultant residue was triturated with diethyl ether, collected by filtration and dried in vacuo to yield 190 as a white solid (111 mg, 46%). 1H NMR 400 MHz (DMSO-d6): δ 8.13-7.98 (2H, m), 7.89 (1H, br s), 7.74-7.58 (2H, m), 7.59-7.39 (4H, m), 7.29-7.14 (1H, m), 5.47 (1H, br s), 3.87-3.77 (2H, m), 3.11 (3H, s). LCMS (Method K): RT=3.72 min, [M+H]+=422

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe resultant residue dissolved in EtOAc (10 mL)
  3. washThe solution was washed with sat. aq. NaHCO3
  4. extractionthe product extracted with EtOAc (3×10 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue was triturated with diethyl ether
  9. filtrationcollected by filtration
  10. customdried in vacuo

Sources & evidence

ORD record
ord-75c7273b798e41228e32958675b2d493
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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