Hydrochloric Acid → HCID 178521311, compound

HRID 2202746Notes

Reaction equation

HRID 2202746 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:45]=[C:46]([F:48])[CH:47]=1)[CH2:5][N:6]([CH2:29][C:30](=[O:44])[C:31]1[CH:35]=[CH:34][N:33](COCC[Si](C)(C)C)[N:32]=1)[C:7]([C:9]1[CH:10]=[N:11][N:12]([C@H:18]2[CH2:23][CH2:22][C@H:21]([C:24]([O:26]CC)=[O:25])[CH2:20][CH2:19]2)[C:13]=1[C:14]([F:17])([F:16])[F:15])=[O:8].Cl>O1CCOCC1>[F:48][C:46]1[CH:45]=[C:4]([CH:3]=[C:2]([F:1])[CH:47]=1)[CH2:5][N:6]([CH2:29][C:30](=[O:44])[C:31]1[CH:35]=[CH:34][NH:33][N:32]=1)[C:7]([C:9]1[CH:10]=[N:11][N:12]([C@H:18]2[CH2:23][CH2:22][C@H:21]([C:24]([OH:26])=[O:25])[CH2:20][CH2:19]2)[C:13]=1[C:14]([F:15])([F:16])[F:17])=[O:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178472416HCID 178472416, compound

Product 1

HCID 178521311HCID 178521311, compoundYield 17.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of compound 8-3 (75 mg, 0.107 mmol) in 1,4-dioxane (2 mL) was added HCl (12 M, 0.5 mL). The mixture was stirred at 80° C. for 2 h. The solvent was removed under reduced pressure. The residue was dissolved in 1,4-dioxane (2 mL) and NH4OH (0.5 mL) was added. The reaction mixture was stirred at room temperature for 2 h. The solvent was removed under reduced pressure and the residue was purified by reverse phase column chromatography (C18 silica gel, 70% CH3CN/water as eluent) to provide the compound of example 8 (10 mg, 16%) as a white solid. 1H NMR (CD3OD) rotamers present δ 7.74-7.50 (2H, m); 6.98-6.95 (1H, m); 6.87-6.78 (3H, m); 5.00 and 4.78 (2H, 2×s); 4.74 and 4.64 (2H, 2×s); 4.28-4.21 (1H, m); 2.36-2.28 (1H, m); 2.17-2.09 (2H, m); 2.02-1.93 (4H, m); 1.62-1.55 (2H, m); LCMS (APCI): 540 (M+H)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in 1,4-dioxane (2 mL)
  3. additionNH4OH (0.5 mL) was added
  4. stirringThe reaction mixture was stirred at room temperature for 2 h
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by reverse phase column chromatography (C18 silica gel, 70% CH3CN/water as eluent)

Sources & evidence

ORD record
ord-f4ea97cf18dc4b8eb6c4f0c531ec1dda
Source dataset
uspto-grants-2016_06
Patent number
US09365522B2

Reaction notes

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