Sodium Hydroxide → HCID 67306607, compound

HRID 1887453Notes

Reaction equation

HRID 1887453 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:12][C:13]2[CH:14]=[N:15][CH:16]=[N:17][CH:18]=2)[CH:11]=1)[C:7]#[N:8])([O-])=O.[Sn](Cl)Cl.[OH-].[Na+]>O1CCOCC1.Cl>[NH2:1][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([O:12][C:13]2[CH:18]=[N:17][CH:16]=[N:15][CH:14]=2)[CH:11]=1)[C:7]#[N:8]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 67307527HCID 67307527, compound

Product 1

HCID 67306607HCID 67306607, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Compound 21 (100 mg, 0.413 mmol, 1.00 eq) was dissolved in Dioxane (2.0 mL) and added to argon purged vial. Tin(II) chloride (390 mg, 2.06 mmol, 5.00 eq) was dissolved in concentrated HCl (0.66 mL) and added to the reaction vial dropwise. The solution stirred at rt for 1 h. The reaction was neutralized with 6N NaOH (2.0 mL) and extracted (3×) with CH2Cl2. The combined organics were dried (MgSO4), filtered, and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 58 mg (67%) of the title compound as a yellow solid: 1H NMR (400 MHz, DMSO-d6) δ 9.04 (s, 1H), 8.68 (s, 2H), 6.71 (t, J=1.5 Hz, 1H), 6.68 (t, J=2.2 Hz, 1H), 6.51 (t, J=2.2 Hz, 1H), 5.86 (s, 2H); ES-MS [M+1]+: 213.1.

Workup

  1. additionadded to argon purged vial
  2. additionadded to the reaction vial dropwise
  3. extractionextracted (3×) with CH2Cl2
  4. dry with materialThe combined organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-9cce7ae60493463f8cdc03b2f7c0bef4
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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