HCID 22607380, compound → HCID 22607631, compound

HRID 2307765Notes

Reaction equation

HRID 2307765 reaction equation
C1(C(C2C=CC=CC=2)=[N:8][C:9]2[CH:10]=[N:11][CH:12]=[C:13]([NH:15][C:16]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:17]=3[CH:18]=[CH:19][N:20]=[CH:21]4)[CH:14]=2)C=CC=CC=1>C1COCC1.O.Cl>[CH:21]1[C:22]2[C:17](=[C:16]([NH:15][C:13]3[CH:12]=[N:11][CH:10]=[C:9]([NH2:8])[CH:14]=3)[CH:25]=[CH:24][CH:23]=2)[CH:18]=[CH:19][N:20]=1

Participants

5

Reactant 1

HCID 22607380HCID 22607380, compound

Product 1

HCID 22607631HCID 22607631, compoundYield 69.4%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 23D (145 mg; 0.36 mmol) in 3 mL THF at room temperature was treated with 10 drops of water and 3 drops of conc. HCl, stirred for 2 hours, and concentrated. The residue was partitioned between ethyl acetate and concentrated NaHCO3 (aq). The aqueous layer was extracted three times 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 10% methanol/dichloromethane to provide the desired product (59 mg, 68%).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between ethyl acetate and concentrated NaHCO3 (aq)
  3. extractionThe aqueous layer was extracted three times 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 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-bf28506b52ea49c690001712c2d7b1fe
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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