Ammonium Chloride → HCID 22614876, compound

HRID 842670Notes

Reaction equation

HRID 842670 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[C:13]([C:27]2[N:31]([CH2:32][C:33](OC)=[O:34])[N:30]=[N:29][N:28]=2)=[C:14]2[C:19](=[CH:20][C:21]=1[Cl:22])[N:18]=[C:17]([O:23][CH3:24])[C:16]([O:25][CH3:26])=[N:15]2.[Cl-].[NH4+]>ClCCl>[Cl:11][C:12]1[C:13]([C:27]2[N:31]([CH2:32][CH2:33][OH:34])[N:30]=[N:29][N:28]=2)=[C:14]2[C:19](=[CH:20][C:21]=1[Cl:22])[N:18]=[C:17]([O:23][CH3:24])[C:16]([O:25][CH3:26])=[N:15]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21225700Diisobutylaluminumhydride3×HCID 22614883HCID 22614883, compound

Product 1

HCID 22614876HCID 22614876, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diisobutylaluminium hydride (1M in tetrahydrofuran, 0.7 mL, 0.7 mmol) was added dropwise to a stirred solution of 6,7-dichloro-2,3-dimethoxy-5-(1-methoxycarbonylmethyl-1H-tetrazol-5-yl)quinoxaline (Preparation 11, 0.126 g, 0.32 mmol) in dichloromethane (15 mL) at −78° C. under nitrogen. After 1 hour, the reaction mixture was allowed to warm to room temperature and diisobutylaluminium hydride (1M in tetrahydrofuran, 0.7 mL, 0.7 mmol) was added, followed 30 minutes later by further diisobutylaluminium hydride (1M in tetrahydrofuran, 0.7 mL, 0.7 mmol). After a further 0.25 hours saturated ammonium chloride solution (20 mL) was added to the mixture and the aqueous phase was extracted with dichloromethane (2×25 mL). The combined organic extracts were washed with brine (50 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with dichloromethane:methanol (99:1, by volume) to give the title compound (93 mg, 79%) as a white solid.

Workup

  1. extractionthe aqueous phase was extracted with dichloromethane (2×25 mL)
  2. washThe combined organic extracts were washed with brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography on silica gel
  6. washeluting with dichloromethane:methanol (99:1, by volume)

Sources & evidence

ORD record
ord-27dfaaef46194b3cb799d33f9c15a64c
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

Loading…