Hydrochloric Acid → HCID 25105913, compound

HRID 657694Notes

Reaction equation

HRID 657694 reaction equation
[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[N:5]=[C:4]([CH3:11])[C:3]=1[C:12]#[C:13][CH:14]([CH:16]1[CH2:21][CH2:20][CH:19]([C:22]([O:24]C)=[O:23])[CH2:18][CH2:17]1)[OH:15].CO.[OH-].[Na+].Cl>O1CCCC1>[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[N:5]=[C:4]([CH3:11])[C:3]=1[C:12]#[C:13][CH:14]([CH:16]1[CH2:21][CH2:20][CH:19]([C:22]([OH:24])=[O:23])[CH2:18][CH2:17]1)[OH:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 25105912HCID 25105912, compound

Product 1

HCID 25105913HCID 25105913, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 65C (26.5 mg, 0.077 mmol) in tetrahydrofuran (0.5 mL)/methanol (0.5 mL) was added 2N NaOH (77 μL, 0.154 mmol). The reaction mixture was stirred at room temperature overnight, and neutralized with 2N HCl (0.154 mmol). It was purified by reverse phase HPLC C-18 column, eluting with a 5-100% CH3CN gradient in 10 mM ammonium acetate(aq.)) to provide the title compound as a white solid (10 mg, 40% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.42 (s, 1H), 8.31 (s, 2H), 5.31 (s, 1H), 4.37 (d, J=5.43 Hz, 1H), 2.49 (s, 3H), 2.48-2.50 (m, 1H), 1.26-2.13 (m, 9H). MS (ESI) m/z 330 (M+H)+.

Workup

  1. customIt was purified by reverse phase HPLC C-18 column
  2. washeluting with a 5-100% CH3CN gradient in 10 mM ammonium acetate(aq.))

Sources & evidence

ORD record
ord-805d20c79d6548e1a588dd99485748f1
Source dataset
uspto-grants-2011_12
Patent number
US08076344B2

Reaction notes

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