Dimethylformamide → HCID 86662435, compound

HRID 2368165Notes

Reaction equation

HRID 2368165 reaction equation
[Cl:1][C:2]1(C(O)=O)[CH:7]=[CH:6][C:5]([Cl:8])=[N:4][NH:3]1.[CH3:12][N:13]([CH:15]=[O:16])C.C(Cl)(=O)C(Cl)=O.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])CN>ClCCl.CN(C1C=CN=CC=1)C>[Cl:8][C:5]1[N:4]=[N:3][C:2]([Cl:1])=[CH:7][C:6]=1[C:15]([NH:13][CH2:12][C:30]1[CH:27]=[CH:26][C:25]([O:24][CH3:23])=[C:32]([O:33][CH3:34])[CH:31]=1)=[O:16]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 79832VeratrylamineHCID 66763845HCID 66763845, compound

Product 1

HCID 86662435HCID 86662435, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,6-dichloropyridazinecarboxylic acid (1-1, 2.0 g, 10.4 mmol, 1.0 equiv) in dichloromethane (26 mL) was added catalytic DMF (0.16 mL, 2.1 mmol, 0.2 equiv) and oxalyl chloride (1.81 mL, 20.7 mmol, 2.0 equiv) at 0° C. The reaction mixture was stirred for 1 hour and concentrated. The crude residue was dissolved in dichloromethane (26 mL) and to the reaction was added 3,4-dimethoxybenzylamine (3.12 mL, 20.7 mmol, 2.0 equiv), TEA (1.81 mL, 20.8 mmol, 2.0 equiv), and DMAP (1.81 mL, 20.8 mmol, 2.0 equiv) at 0° C. The reaction mixture became cloudy with precipitate and was stirred 24 hours at ambient temperature. The reaction was partitioned between EtOAc and saturated NaHCO3. The organic phase was washed with NaHCO3, water and brine and dried over MgSO4. After concentration, the residue was purified by normal phase column chromatography (5 to 85% EtOAc in hexanes) to afford the product (1-2) as a yellow solid. ESI+MS [M+H]+ C14H13Cl2N3O3: 342.1 found, 342.0 required.

Workup

  1. concentrationconcentrated
  2. dissolutionThe crude residue was dissolved in dichloromethane (26 mL) and to the reaction
  3. stirringwas stirred 24 hours at ambient temperature
  4. customThe reaction was partitioned between EtOAc and saturated NaHCO3
  5. washThe organic phase was washed with NaHCO3, water and brine
  6. dry with materialdried over MgSO4
  7. concentrationAfter concentration
  8. customthe residue was purified by normal phase column chromatography (5 to 85% EtOAc in hexanes)

Sources & evidence

ORD record
ord-6e5bc157261f45a2a83e6674ec91e129
Source dataset
uspto-grants-2014_04
Patent number
US08703770B2

Reaction notes

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