Hydrochloric Acid → HCID 178503026, compound

HRID 1525347Notes

Reaction equation

HRID 1525347 reaction equation
[OH:1][C:2]1[C:7]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([P:19]([CH3:24])(=[O:23])[O:20]CC)=[CH:15][CH:14]=3)[CH:9]=2)=[CH:6][N:5]=[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[N:3]=1.[OH-].[Na+].Cl>O1CCOCC1.O>[OH:1][C:2]1[C:7]([C:8]2[O:12][N:11]=[C:10]([C:13]3[CH:18]=[CH:17][C:16]([P:19]([CH3:24])(=[O:20])[OH:23])=[CH:15][CH:14]=3)[CH:9]=2)=[CH:6][N:5]=[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178476753HCID 178476753, compound

Product 1

HCID 178503026HCID 178503026, compoundYield 1.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of compound 38-g (150 mg, 0.35 mmol) in dioxane (5 mL) was added 3 N NaOH aqueous solution (2 mL). The reaction mixture was refluxed for 1 h, and diluted with water, adjusted pH to 2 with concentrated HCl. The reaction mixture was concentrated and purified by pre-HPLC to afford compound 38-1 (2 mg). 1H NMR (300 MHz, CD3OD) δ 8.84-8.56 (m, 1H), 8.77 (s, 1H), 8.44-8.46 (m, 1H), 8.10-8.14 (m, 3H), 7.89-7.95 (m, 2H), 7.70-7.77 (m, 2H), 7.34 (s, 1H), 7.00-7.16 (d, J=51.3 Hz, 1H), 1.57-1.62 (d, J=14.4 Hz, 3H). LC-MS 395 [M+H]+

Workup

  1. temperatureThe reaction mixture was refluxed for 1 h
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by pre-HPLC

Sources & evidence

ORD record
ord-1c2e1e3941cc420c86bc13f3f781cd92
Source dataset
uspto-grants-2015_07
Patent number
US09079930B2

Reaction notes

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