Hydrochloric Acid → HCID 12129623, compound

HRID 2253333Notes

Reaction equation

HRID 2253333 reaction equation
[I:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][O:7][CH:8]([C:17]2[N:21]([CH3:22])[CH:20]=[N:19][CH:18]=2)[C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=2)=[C:4]([N+:25]([O-])=O)[CH:3]=1.O.O.Cl[Sn]Cl.Cl>CO>[NH2:25][C:4]1[CH:3]=[C:2]([I:1])[CH:24]=[CH:23][C:5]=1[CH2:6][O:7][CH:8]([C:17]1[N:21]([CH3:22])[CH:20]=[N:19][CH:18]=1)[C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 17965955HCID 17965955, compound

Product 1

HCID 12129623HCID 12129623, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example 46B (0.8 g, 2.1 mmol) in methanol (50 mL) at room temperature was treated with SnCl2.2H2O (1.41 g, 6.3 mmol) and concentrated HCl (20 mL), stirred for 12 hours, and concentrated. The concentrate was treated with aqueous NaOH and extracted with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by flash column chromatography on silica gel with CH2Cl2:CH3OH:NH4OH (100:3:3, v/v) to provide the desired product. MS (DCI/NH3) m/z 445 (M+H)+.

Workup

  1. concentrationconcentrated
  2. additionThe concentrate was treated with aqueous NaOH
  3. extractionextracted with ethyl acetate
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe concentrate was purified by flash column chromatography on silica gel with CH2Cl2:CH3OH:NH4OH (100:3:3

Sources & evidence

ORD record
ord-1085e11bbebc43c684fe4c30934f84ba
Source dataset
uspto-grants-2008_01
Patent number
US07323570B2

Reaction notes

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