HCID 18317237, compound → HCID 9929959, compound

HRID 1700129Notes

Reaction equation

HRID 1700129 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[N:9][C:10]([CH:23]3[CH2:28][CH2:27][N:26](C(OCC4C=CC=CC=4)=O)[CH2:25][CH2:24]3)=[CH:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)=[CH:3][CH:2]=1.Br.CC(O)=O>Cl>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[N:9][C:10]([CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)=[CH:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:21])([F:20])[F:22])[CH:14]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 18317237HCID 18317237, compoundHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 9929959HCID 9929959, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Under Ar, a mixture of 35 (0.68 g, 1.3 mmol) and 30% HBr—AcOH (10 mL) was stirred at room temperature. After 3 h, 3N HCl (50 mL) was added and the solution extracted with Et2O (2×). The aqueous layer was basified with saturated Na2CO3 and extracted with EtOAc (6×). The organic extracts were dried, filtered and concentrated to dryness. The residue was crystallzed from EtOAc-hexanes to yield 73 mg (15%) of 36 mp 148-50° C.

Workup

  1. extractionthe solution extracted with Et2O (2×)
  2. extractionextracted with EtOAc (6×)
  3. customThe organic extracts were dried
  4. filtrationfiltered
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-da2024370c55463e99af01be2661b7ce
Source dataset
uspto-grants-2002_02
Patent number
US06350744B1

Reaction notes

Loading…