Hydrochloric Acid → HCID 54575253, compound

HRID 2096274Notes

Reaction equation

HRID 2096274 reaction equation
[O:1]=[C:2]1[NH:7][CH:6]=[C:5]([CH2:8][C:9]2[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=2)[C:12]([O:14]CC)=[O:13])[N:4]2[CH:20]=[C:21]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[CH:22]=[C:3]12.[OH-].[Na+].Cl>O1CCCC1.O>[O:1]=[C:2]1[NH:7][CH:6]=[C:5]([CH2:8][C:9]2[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=2)[C:12]([OH:14])=[O:13])[N:4]2[CH:20]=[C:21]([C:23]3[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=3)[CH:22]=[C:3]12

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54575250HCID 54575250, compound

Product 1

HCID 54575253HCID 54575253, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a suspension of EXAMPLE 4E (30 mg, 0.08 mmol) in tetrahydrofuran (5 mL) was added NaOH (32 mg, 0.8 mmol) in water (0.5 ml). The reaction mixture was heated at 80° C. overnight. After cooling, the reaction mixture was neutralized with 1N aqueous HCl, and concentrated. The residue was separated by HPLC (0-100% gradient CH3CN in water containing 0.1% CF3CO2H to afford the title compound. MS (DCI/NH3) m/z 346 (M+H)+; 1H NMR (300 MHz, dimethylsulfoxide-d6): δ 4.19 (s, 2H), 6.59 (d, J=5.55 Hz, 1H), 7.47 (t, J=7.54 Hz, 1H), 7.68 (d, J=7.54 Hz, 1H), 7.77 (d, J=1.59 Hz, 1H), 7.82 (d, J=7.93 Hz, 1H), 7.97 (s, 1H), 8.19 (d, J=6.74 Hz, 2H), 8.33 (d, J=1.59 Hz, 1H), 8.73 (d, J=6.35 Hz, 2H), 10.74 (d, J=5.55 Hz, 1H), 12.98 (s, 1H).

Workup

  1. temperatureAfter cooling
  2. concentrationconcentrated
  3. customThe residue was separated by HPLC (0-100% gradient CH3CN in water containing 0.1% CF3CO2H

Sources & evidence

ORD record
ord-de234c6b343745ec8478c929578b90f6
Source dataset
uspto-grants-2013_05
Patent number
US08450320B2

Reaction notes

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