Hydrochloric Acid → HCID 18317251, compound

HRID 1700126Notes

Reaction equation

HRID 1700126 reaction equation
[CH3:1][CH:2]([NH:9][C:10]1[N:15]=[C:14]([C:16]2[N:17]=[N:18][C:19]([CH:32]3[CH2:37][CH2:36][N:35](C(OCC4C=CC=CC=4)=O)[CH2:34][CH2:33]3)=[CH:20][C:21]=2[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[CH:13]=[CH:12][N:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl>Br.CC(O)=O>[CH3:1][CH:2]([NH:9][C:10]1[N:15]=[C:14]([C:16]2[N:17]=[N:18][C:19]([CH:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)=[CH:20][C:21]=2[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:29])([F:31])[F:30])[CH:23]=2)[CH:13]=[CH:12][N:11]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18317240HCID 18317240, compound

Product 1

HCID 18317251HCID 18317251, compoundYield 29.5%

Reagents, catalysts & solvents 1

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidSolvent

Procedure

Under Ar, a solution of 29 (0.3 g, 0.47 mmol) in 30% HBr-AcOH (5 mL) was stirred at room temperature for 1 h. The reaction was then treated with 2N HCl and extracted with Et2O (2×). The resulting aqueous was then basified with saturated Na2CO3 and extracted with EtOAc (3×). The organic extracts were dried, filtered and concentrated to dryness. The residue was chromatographed on a Still column (40 mm) and the product eluted with 5% CH3OH CHCl3 saturated with NH3 to yield 70 mg of 30.

Workup

  1. extractionextracted with Et2O (2×)
  2. extractionextracted with EtOAc (3×)
  3. customThe organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was chromatographed on a Still column (40 mm)
  7. washthe product eluted with 5% CH3OH CHCl3 saturated with NH3

Sources & evidence

ORD record
ord-1c5bfa277a3a451c926f097ceac43545
Source dataset
uspto-grants-2002_02
Patent number
US06350744B1

Reaction notes

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