HCID 68157522, compound → HCID 178498687, compound

HRID 243369Notes

Reaction equation

HRID 243369 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:11]([C@@H:20]([NH:22][C:23]3[N:31]=[CH:30][N:29]=[C:28]4[C:24]=3[N:25]=[CH:26][N:27]4C3CCCCO3)[CH3:21])=[N:10][C:9]=2[CH:8]=[CH:7][C:6]=1[F:38])=[O:4]>CO.Cl.O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[C:13]2[N:12]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:11]([CH:20]([NH:22][C:23]3[N:31]=[CH:30][N:29]=[C:28]4[C:24]=3[N:25]=[CH:26][NH:27]4)[CH3:21])=[N:10][C:9]=2[CH:8]=[CH:7][C:6]=1[F:38])=[O:4]

Participants

5

Reactant 1

HCID 68157522HCID 68157522, compound

Product 1

HCID 178498687HCID 178498687, compoundYield 50.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-fluoro-3-phenyl-2-{(S)-1-[9-(tetrahydropyran-2-yl)-9H-purin-6-ylamino]ethyl}-3H-benzoimidazole-4-carboxylic acid methyl ester (50 mg, 0.097 mmol) in MeOH (2 mL) and 4N HCl in dioxane (0.5 ml) was stirred at RT for 30 min then the volatiles were removed under reduced pressure. The resulting residue was dissolved in a minimum amount of MeOH and EtOAc. A solid precipitated on standing and was collected by filtration to afford 197 (21 mg, 46%). LCMS (Method K): RT 3.28 min [M+H]+ 432.1. 1H NMR (DMSO-d6, 400 MHz): δ 12.65 (1H, s), 9.92 (1H, br s), 8.61 (1H, s), 8.50 (1H, s), 7.89 (1H, dd, J=8.90, 4.75 Hz), 7.59-7.48 (2H, m), 7.45-7.30 (3H, m), 7.25 (1H, dd, J=10.49, 8.90 Hz), 5.51-5.40 (1H, m), 3.09 (3H, s), 1.65 (3H, d, J=6.84 Hz)

Workup

  1. customthe volatiles were removed under reduced pressure
  2. dissolutionThe resulting residue was dissolved in a minimum amount of MeOH and EtOAc
  3. customA solid precipitated
  4. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-ed4f6c2a1df34c2d92ec1b18ac568a47
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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