Trimethylamine oxide → HCID 22614849, compound

HRID 842669Notes

Reaction equation

HRID 842669 reaction equation
C12BC(CCC1)CCC2.[Cl:10][C:11]1[C:12]([C:26]2[N:30]([CH2:31][CH:32]=[CH2:33])[N:29]=[N:28][N:27]=2)=[C:13]2[C:18](=[CH:19][C:20]=1[Cl:21])[N:17]=[C:16]([O:22][CH3:23])[C:15]([O:24][CH3:25])=[N:14]2.C[N+]([O-:38])(C)C>O1CCCC1>[Cl:10][C:11]1[C:12]([C:26]2[N:30]([CH2:31][CH2:32][CH2:33][OH:38])[N:29]=[N:28][N:27]=2)=[C:13]2[C:18](=[CH:19][C:20]=1[Cl:21])[N:17]=[C:16]([O:22][CH3:23])[C:15]([O:24][CH3:25])=[N:14]2

Participants

5

Reactant 3

HCID 1145Trimethylamine oxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 22614845HCID 22614845, compound

Product 1

HCID 22614849HCID 22614849, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

9-Borabicyclo[3.3.1]nonane (0.5M in tetrahydrofuran, 9.1 mL, 4.55 mmol) was added dropwise to a stirred suspension of 6,7-dichloro-2,3-dimethoxy-5-(1-allyl-1H-tetrazol-5-yl)quinoxaline (Preparation 19, 0.67 g, 1.82 mmol) in dry tetrahydrofuran (15 mL) at room temperature under nitrogen. The reaction mixture was heated under reflux for 18 hours, trimethylamine-N-oxide (1.03 g, 13.7 mmol) was added portionwise to the cooled reaction mixture and the mixture was heated under reflux for 2 hours then concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, by gradient elution using dichloromethane:methanol (100:0 changing to 99.5:0.5, by volume) to give the title compound (0.510 g, 73%) as a white solid, mp 188-189° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 18 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 2 hours
  5. concentrationthen concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel, by gradient elution

Sources & evidence

ORD record
ord-fa021e5af5ac46ef94633a3e0e33e9c6
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

Loading…