Water → HCID 22614889, compound

HRID 842684Notes

Reaction equation

HRID 842684 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[C:13]([N:27]2[C:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[N:30][N:29]=[C:28]2[C:38](OCC)=[O:39])=[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+].O>ClCCl>[Cl:11][C:12]1[C:13]([N:27]2[C:31]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[N:30][N:29]=[C:28]2[CH2:38][OH:39])=[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

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 21225700Diisobutylaluminumhydride2×HCID 22614907HCID 22614907, compound

Product 1

HCID 22614889HCID 22614889, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diisobutylaluminium hydride (1M in tetrahydrofuran, 2.5 mL, 2.5 mmol) was added to a solution of 6,7-dichloro-2,3-dimethoxy-5-(3-ethoxycarbonyl-5-phenyl-4H-1,2,4-triazol-4-yl)quinoxaline (Preparation 93, 237 mg, 0.5 mmol) in dichloromethane (10 mL) at room temperature under nitrogen. After 1 hour, a further portion of diisobutylaluminium hydride (1M in tetrahydrofuran, 1 mL, 1 mmol) was added, the mixture was stirred for a further 1 hour, then saturated aqueous ammonium chloride solution (10 mL) was added. Dichloromethane (50 mL) and water (50 mL) were added and the mixture was filtered through ARBOCEL (trade mark), washing the residue with warm dichloromethane:methanol (9:1, by volume, 100 mL). The organic layer was separated, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel, by gradient elution using hexane:ethyl acetate:methanol (1:1:0 changing to 0:1:0 changing to 0:95:5, by volume) to give the title compound (70 mg, 79%) as an off-white solid.

Workup

  1. filtrationthe mixture was filtered through ARBOCEL (trade mark)
  2. washwashing the residue with warm dichloromethane:methanol (9:1, by volume, 100 mL)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel, by gradient elution

Sources & evidence

ORD record
ord-3880b71eb9334c1ab15c2b626fd71a52
Source dataset
uspto-grants-2002_04
Patent number
US06376490B1

Reaction notes

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