Acetic Acid → (S)-3,5-dichloro-4-(2-(3,4-dimethoxyphenyl)-2-((4-(hydroxymethyl)benzoyl)oxy)ethyl)pyridine 1-oxide

HRID 2284852Notes

Reaction equation

HRID 2284852 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:32])[CH:5]=[C:6]([Cl:31])[C:7]=1[CH2:8][C@@H:9]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)[O:10][C:11](=[O:20])[C:12]1[CH:17]=[CH:16][C:15]([CH:18]=[O:19])=[CH:14][CH:13]=1.NC1N=NC=CC=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:31][C:6]1[CH:5]=[N+:4]([O-:32])[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C@@H:9]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)[O:10][C:11](=[O:20])[C:12]1[CH:13]=[CH:14][C:15]([CH2:18][OH:19])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 230373AminopyridazineHCID 5049666Sodium triacetoxyborohydrideHCID 86720687(S)-3,5-dichloro-4-(2-(3,4-dimethoxyphenyl)-2-((4-formylbenzoyl)oxy)ethyl)pyridine 1-oxide

Product 1

HCID 118114214(S)-3,5-dichloro-4-(2-(3,4-dimethoxyphenyl)-2-((4-(hydroxymethyl)benzoyl)oxy)ethyl)pyridine 1-oxideYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (S)-3,5-dichloro-4-(2-(3,4-dimethoxyphenyl)-2-((4-formylbenzoyl)oxy)ethyl)pyridine 1-oxide (412 mg, 0.87 mmol) in DCM (10 mL) was added 3-aminopyridazine (165 mg, 1.73 mmol) followed by glacial acetic acid (150 μL, 2.61 mmol). The reaction was stirred at room temperature for 30 minutes then NaB(OAc)3H (551 mg, 2.61 mmol) was added. The reaction mixture was stirred at room temperature for 18 hours. The reaction was diluted with DCM (10 mL) and quenched with water. The organic phase was washed with saturated aqueous NaHCO3 solution, filtered through hydrophobic fit and evaporated to dryness. The residue was triturated with DCM (2 mL) and CH3CN (5 mL). The solid was collected by filtration, washed with DCM and dried to provide the title compound (300 mg, 72%) as white solid.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 18 hours
  2. customquenched with water
  3. washThe organic phase was washed with saturated aqueous NaHCO3 solution
  4. filtrationfiltered through hydrophobic fit
  5. customevaporated to dryness
  6. customThe residue was triturated with DCM (2 mL) and CH3CN (5 mL)
  7. filtrationThe solid was collected by filtration
  8. washwashed with DCM
  9. customdried

Sources & evidence

ORD record
ord-10fa87adaa6346a7ade1ce22fb52b922
Source dataset
uspto-grants-2015_09
Patent number
US09145409B2

Reaction notes

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